How to hide a structure revision efficiently ?

How to "sell" the same data twice to the community ?

The Timeline Received Accepted Published	Publication Corresponding Author	Title	Remarks All Searches of the CAS-Registry File were performed on 2018-02-26
Received: 2005-01-11 On Web: 2005-02-11	Org.Lett., 7, 1117 - 1119 (2005) Christian V. Stevens	Straightforward Ring Expansion of Pyroglutamates to Perhydro-1,3-diazepine-2,4-diones	Supplementary Material available: "All carbon spectra of the new compounds synthesized and their complete characterization." ¹³C-NMR spectral data of compounds numbered as "Table 1, entry 1 to 8" are given All 8 compounds shown are [1,3]-diazepin-derivatives containing a 7-membered cyclic system 16 Substances described; 8 of them contain a 7-membered ring system Structural overlap: 4 (ChemComm) + 8 (EurJOrgChem)
Received: 2005-06-20 Accepted: 2005-07-14 On Web: 2005-08-04	Chem.Commun., 2005, 4477 - 4478 Christian V. Stevens	Synthesis of 1,3-dioxo-hexahydropyrido[1,2-c][1,3]diazepine carboxylates, a new bicyclic skeleton formed by ring expansion-RCM methodology	"1,3-Diazepan- 2,4-diones, or perhydro-1,3-diazepine-2,4-diones, however, are rare and no straightforward synthetic method for their preparation existed until recently we discovered that this interesting skeleton can be prepared in one step by intramolecular transamidation of pyroglutamates after reaction with isocyanates" [Publication: Org.Lett.,7,1117 - 1119(2005) 43 Substances described; 21 out of them contain a 7-membered ring system Structural overlap: 4 (OrgLett) + 18 (EurJOrgChem)
On Web: 2005-10-14	Org.Lett., 7, 5347 (2005) Christian V. Stevens	Additions and Correction	"The incorrect product was reported in this paper. X-ray analysis after publication shows that the products are not perhydro-1,3-diazepine-2,4-diones, but are hydantoins which were formed by a ring-closing-ring-opening sequence and which have almost identical NMR spectra." "A paper is in preparation stating this misinterpretation and proving the structure of the hydantoins by X-ray analysis."
On Web: 2005-12-15	Chem.Commun., 2005, 4477 - 4478	Additions and Correction	"An incorrect product was reported in this article. After publication, X-ray analysis showed that the products formed by reaction of pyroglutamates 1 with isocyanates are not perhydro-1,3-diazepine-2,4-diones 2, but are hydantoins 3 which are formed by a ring closing-ring opening sequence and which have almost identical NMR spectra. As a consequence, the RCM products synthesised (Scheme 3) are in fact bicyclic hydantoin derivatives 4." "A full paper is in preparation stating this misinterpretation and proving the structure of the hydantoins by X-ray analysis."
Received: 2006-01-20 On Web: 2006-04-03	Eur. J. Org. Chem., 2006, 2649-2660 Christan V. Stevens	The Pyroglutamate Hydantoin Rearrangement	57 Substances described; 0 out of them contain a 7-membered ring system Structural overlap: 8 (Orglett) + 18 (ChemComm) Org.Lett., 7, 1117 - 1119(2005) not cited Chem.Commun., 2005, 4477 - 4478 not cited
Intermediate Summary A reaction didn't work as expected The spectrum interpretation was in error The authors recognized this wrong structure elucidation In both journals a correction has been published Within these corrections an upcoming publication is announced proving the new structure proposals (hydantoins instead of perhydro-1,3-diazepine-2,4-diones) proven by X-ray analysis From the timeline given above it can be deduced that this error was known to the community on October 14^th, 2005; second revision was published on December 15^th, 2005 Till Dec 15^th, 2005: Errors might happen - perfect error handling What can be found afterwards in the promised paper, obviously Eur. J. Org. Chem., 2006, 2649-2660
Now we start analyzing how these publications are cited in the literature All Searches of the CAS-Registry File using SciFinder were performed on 2018-02-26
Org.Lett.,7,1117 - 1119(2005)	7 citations	2 citations by C. V. Stevens	Chem.Commun., 2005, 4477 - 4478 / Paper announced to be corrected J. Org. Chem., 71, 3863-3868 (2006) / Citation (25) - only with repect to an experimental detail The above-mentioned JOC-paper has been received on 2006-02-22, at this time the necessity for a structure revision was already known and the EuJOC-paper - showing hydantoines instead of diazepinediones - was submitted 4 weeks before ! The following statement in this paper is very interesting: "Recently, we described the pyroglutamate-hydantoin rearrangement.(Eur.J.Org.Chem.,in press) It was found that treating pyroglutamates 3 with NaH in the presence of isocyanates or isothiocyanates in THF produces hydantoins 4 in high yield via a ring-closing-ring-opening sequence." The ring expansion from Pyroglutamates to 1,3-diazepin-derivatives is now a pyroglutamate-hydantoin rearrangement published in Eur. J. Org. Chem., 2006, 2649-2660 Let's analyze this publication below
Correction of Org. Lett., 7, 1117 - 1119 (2005)	1 citation	0 citations by C. V. Stevens	Cited from: Magn. Reson. Chem., 45, 240 - 244 (2007) .... they [the compounds] were actually hydantoins, which agrees with their more recent conclusion from X-ray data
Chem.Commun., 2005, 4477 - 4478	9 citations	0 citations by C. V. Stevens
Eur. J. Org. Chem., 2006, 2649-2660	19 citations	2 citations by C. V. Stevens

Comparison of ¹³C-NMR Data Assigned lines as given in the publication are superimposed by a green rectangle Ambigiously assigned lines as given in the publication are superimposed by a yellow rectangle Ambigiously assigned lines are assigned to a specific carbon by us during data-input, because of slightly different information (e.g. C_ar versus C_o,m) slightly different assignments in the display may be obtained - nevertheless the peaklist remains identical and the exchange-groups are kept as given in the publication
CSEARCH: UWLU-062227 Compound "Table 1 / Entry 1" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043579 Compound 9A Eur.J.Org.Chem.,2006,2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Identical melting point Structure revision Original literature not cited

CSEARCH: UWLU-062228 Compound "Table 1 / Entry 2" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043580 Compound 9B Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-062229 Compound "Table 1 / Entry 3" Org.Lett., 7, 1117 - 1119 (2005) 8 aromatic lines expected; 4 given Melting point: 167^oC	CSEARCH: UWLU-043581 Compound 9C Eur.J.Org.Chem., 2006, 2649-2660 8 aromatic lines expected; 8 given Melting point: 157^oC	Schematic spectra

		Identical ¹H-NMR data Slightly different ¹³C-NMR data - see header Identical IR-data Melting point different - see header Structure revision Original literature not cited

CSEARCH: UWLU-062230 Compound "Table 1 / Entry 4" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043582 Compound 9D Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Identical melting point Structure revision Original literature not cited

CSEARCH: UWLU-062231 Compound "Table 1 / Entry 5" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043583 Compound 9E Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Identical melting point Structure revision Original literature not cited

CSEARCH: UWLU-062232 Compound "Table 1 / Entry 6" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043584 Compound 9F Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-062233 Compound "Table 1 / Entry 7" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043585 Compound 9G Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-062234 Compound "Table 1 / Entry 8" Org.Lett., 7, 1117 - 1119 (2005)	CSEARCH: UWLU-043586 Compound 9H Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Identical melting point Structure revision Original literature not cited

CSEARCH: UWLU-100153 ETHYL-4-ALLYL-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043587 Compound 13A Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100152 ETHYL-4-ALLYL-2,7-DIOXO-1-PHENYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043588 Compound 13B Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100154 ETHYL-4-ALLYL-2,7-DIOXO-1-BENZYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043589 Compound 13C Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100156 ETHYL-4-[2-CHLOROPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043590 Compound 13D Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100155 ETHYL-4-[2-METHYLPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043591 Compound 13E Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100157 Ethyl 3,4-diallyl-2,7-dioxo-1-propyl-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043594 Compound 14A Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100158 Ethyl 3,4-diallyl-2,7-dioxo-1-phenyl-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043595 Compound 14B Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100160 Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043596 Compound 14C Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100159 Ethyl 4-allyl-3-(2-methylprop-2-enyl)-1-phenyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043597 Compound 14D Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100162 Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043598 Compound 14E Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100161 Ethyl-4-allyl-1-benzyl-3-[2-(ethoxycarbonyl)prop-2-enyl]-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043599 Compound 14F Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Chemical shift values are always sorted - both peaklists show a sequence of 2.60 / 2.52 / 4.02-4.16 ppm Identical ¹³C-NMR data In both ¹³C-NMR data sets 1 signal is missing - 2 olefinic CH₂ in structure; only 1 signal is given Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100164 Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043600 Compound 14G Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100163 Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043601 Compound 14H Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100167 Ethyl-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043602 Compound 15A Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100166 Ethyl-1,3-dioxo-2-phenyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043603 Compound 15B Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100171 Ethyl 2-benzyl-8-chloro-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043604 Compound 15C Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100165 Ethyl 8-methyl-1,3-dioxo-2-phenyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043605 Compound 15D Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100169 Ethyl 2-benzyl-8-(chloromethyl)-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-43606 Compound 15E Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100168 Diethyl 2-benzyl-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a,8(1H)-dicarboxylate Chem.Commun., 2005, 4477 - 4478 "Instead of the second generation Grubbs^TM catalyst, the second generation Hoveyda-Grubbs^TM catalyst was used for this reaction" "Chromatography: first Hex/EtOAc (3/1) untill R_f = 0.26, then strip with EtOAc + 5% CH₂Cl₂"	CSEARCH: UWLU-043607 Compound 15F Eur.J.Org.Chem., 2006, 2649-2660 "Instead of the second generation Grubbs^TM catalyst, the second generation Hoveyda-Grubbs^TM catalyst is used for this reaction" "Chromatography: first Hex/EtOAc (3:1) until R_f = 0.26, then strip with EtOAc + 5 % CH₂Cl₂"	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

CSEARCH: UWLU-100172 Ethyl 7-chloro-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043608 Compound 15G Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra

		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited
CSEARCH: UWLU-100170 Ethyl 7-methyl-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate Chem.Commun., 2005, 4477 - 4478	CSEARCH: UWLU-043609 Compound 15H Eur.J.Org.Chem., 2006, 2649-2660	Schematic spectra


		Identical ¹H-NMR data Identical ¹³C-NMR data Identical IR-data Structure revision Original literature not cited

My Summary and Conclusion

Org. Lett., 7, 1117 (2005): 8 Structures are wrong

Chem.Commun., 2005, 4477-4478: 21 Structures are wrong

The wrong structures are known to the authors latest on Oct 14^th, 2005 - first correction in Org.Lett. is available online; correction in Chem.Commun. follows on Dec 15^th, 2005

In both journals the correction of the wrong structures based on XRAY-investigations is announced as upcoming full paper

Eur.J.Org.Chem., 2006, 2649-2660: 29 Structures have been revised

The necessity of a structure revision is known since Oct 14^th, 2005 - The EuJOC-paper has been received on Jan 20^th, 2006 - plenty of time to insert the structure revision or the citation(s) into this manuscript

The XRAY-derived structure of compound 15b is discussed in detail - no relevant publication holding the wrong structure proposals is cited

There is no hint that the EuJOC-paper is a structure revision of 29 compounds

Neither the paper from "Organic Letters" nor from "Chemical Communications" is cited in the EuJOC-paper

This "strange" style of citing continues in the JOC-paper - again plenty of time to point to the wrong structure elucidation

The spectral data have been obviously transfered by copy/paste with slight variations in their presentation in order to follow journal-specific style rules

The distinction between the 2 classes of compounds (hydantoins versus diazepinediones) is not trivial using NMR-data

Finding this "hidden structure revision" is nearly impossible using common tools - neither a (partial) structure search using CAS-Registry/SciFinder nor using a search strategy based on "cited references" shows this structure revision

All manuscripts have successfully passed the journal-specific 'peer-reviewing' procedure - no surprise: According to my opinion all reviewers had no chance to detect this inconcistency

All publications follow obviously the 'Ethical Guidelines/Code of Conduct' of the publisher - main responsibility is with the author(s). The revisions and the missing citations are not easy to detect

A few facts summarized by an (to me unknown) external expert selected by EuJOC

External Expert	My opinion
Analyzed the original spectra including HMBC provided by Prof. Stevens No hint for misinterpretation of the spectra	I was always convinced that the distinction between these 2 classes of compounds using NMR-data is an extremely difficult question Both proposals fit very well the published C-NMR data, which have been checked very carefully when we added them into the CSEARCH-database - no error recognized by us during data input (valid for all 3 papers)
The error made can happen to everybody	I fully agree - never complaint about this
An upcoming paper is announced in both corrections clarifying this misinterpretation There is neither a citation of the previous work nor a hint given in the text in the EuJOC-paper	I fully agree - this is my complaint
Five compounds checked in detail - identical spectral data are given The arguments used to prove the structure of the diazepines are repeated to prove the structures of the hydantoins	I fully agree - this is my complaint

My Impression: A well hidden structure revision, but not good enough
to avoid detection by CSEARCH
Only detectable when the data of all 3 involved papers are electronically available

How to find this type of well-hidden structure revisions ?

Search for identical spectra associated with different compounds
published by at least one common author in different journals.

This example shows the necessity of automatic peer-reviewing of experimental data and
the urgent need of public domain spectral repositories.

Statement from Prof. Stevens

Additions and Corrections: Eur.J.Org.Chem.

Page written by: Wolfgang Robien
Wolfgang.Robien(-at-)c13nmr.at
This is my opinion and does not necessarily reflect the opinion of the University of Vienna or its representatives

Page written on: Feb 26^th - Feb 28^th, 2018
Page online since (password-protected): Mar 8^th, 2018
Page online since (public): Jun 22^th, 2018
Last modification: Jun 20^th, 2018

Page optimized for a screen-resolution of 1920x1080

History of this webpage

Date	Activity & Remarks

Feb 26^th, 2018	Calculations performed - first part of webpage written
Feb 26^th, 2018	CAS-Searches using SCIFINDER performed
Feb 27^th, 2018	Page continued; Pictures inserted
Feb 28^th, 2018	Page finished
Mar 1^st, 2018	Impressum & Table showing History added
Mar 5^th, 2018	Final Layout
Mar 5^th, 2018	Spectral data checked manually
Mar 5^th, 2018	Summary and Conclusion added
Mar 8^th, 2018	Final layout & upload to server
Mar 8^th, 2018	On server: This webpage is password-protected

FRI, Mar 9^th, 2018 / 10:25 (CET)	Information about this webpage send to the Editorial Offices of "Organic Letters", "Chemical Communications" and "European Journal of Organic Chemistry"

MON, Mar 12^th, 2018 / 16:03 (CET)	Response from "European Journal of Organic Chemistry" received
MON, Mar 12^th, 2018 / 16:36 (CET)	Response from "Chemical Communications" received
WED, Mar 14^th, 2018 / 17:59 (CET)	Response from "Organic Letters" received

All three Editorial Offices contacted the author and stated a positive response from the author to clarify this situation

THU, Apr 12^th, 2018 / 16:45 (CET)	European Journal of Organic Chemistry: Webpage will be peer-reviewed
SUN, Jun 10^th, 2018 / 12:42 (CET)	European Journal of Organic Chemistry: Report from reviewer received
TUE, Jun 19^th, 2018 / 14:16 (CET)	Statement from Prof. Stevens received (via Editorial Office - EuJOC)
TUE, Jun 19^th, 2018 / 21:46 (CET)	Statement from Prof. Stevens directly received
TUE, Jun 19^th, 2018	It is agreed by all involved parties to publish a common statement as soon as possible in the "European Journal of Organic Chemistry" Link will be added here when available
WED, Jun 20^th, 2018	Statement from Prof. Stevens added Final improvements and layout of webpage done Most decisive facts from the reviewer report added and commented

FRI, Jun 22^nd, 2018 / 12:00 (CET)	Password-protection disabled Webpage linked and published

How to hide a structure revision efficiently ?

How to "sell" the same data twice to the community ?

The Timeline

ReceivedAcceptedPublished

PublicationCorresponding Author

Title

Remarks

All Searches of the CAS-Registry File were performed on 2018-02-26

Intermediate Summary

Till Dec 15th, 2005: Errors might happen - perfect error handling

What can be found afterwards in the promised paper, obviously Eur. J. Org. Chem., 2006, 2649-2660

Now we start analyzing how these publications are cited in the literature

All Searches of the CAS-Registry File using SciFinder were performed on 2018-02-26

Comparison of 13C-NMR Data

CSEARCH: UWLU-062227Compound "Table 1 / Entry 1"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043579Compound 9AEur.J.Org.Chem.,2006,2649-2660

Schematic spectra

CSEARCH: UWLU-062228Compound "Table 1 / Entry 2"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043580Compound 9BEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-062229Compound "Table 1 / Entry 3"Org.Lett., 7, 1117 - 1119 (2005) 8 aromatic lines expected; 4 given Melting point: 167oC

CSEARCH: UWLU-043581Compound 9CEur.J.Org.Chem., 2006, 2649-2660 8 aromatic lines expected; 8 given Melting point: 157oC

Schematic spectra

CSEARCH: UWLU-062230Compound "Table 1 / Entry 4"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043582Compound 9DEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-062231Compound "Table 1 / Entry 5"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043583Compound 9EEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-062232Compound "Table 1 / Entry 6"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043584Compound 9FEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-062233Compound "Table 1 / Entry 7"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043585Compound 9GEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-062234Compound "Table 1 / Entry 8"Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043586Compound 9HEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100153 ETHYL-4-ALLYL-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043587Compound 13AEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100152 ETHYL-4-ALLYL-2,7-DIOXO-1-PHENYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043588Compound 13BEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100154 ETHYL-4-ALLYL-2,7-DIOXO-1-BENZYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043589Compound 13CEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100156 ETHYL-4-[2-CHLOROPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043590Compound 13DEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100155 ETHYL-4-[2-METHYLPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043591Compound 13EEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100157 Ethyl 3,4-diallyl-2,7-dioxo-1-propyl-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043594Compound 14AEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100158 Ethyl 3,4-diallyl-2,7-dioxo-1-phenyl-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043595Compound 14BEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100160 Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043596Compound 14CEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100159 Ethyl 4-allyl-3-(2-methylprop-2-enyl)-1-phenyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043597Compound 14DEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100162 Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043598Compound 14EEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100161 Ethyl-4-allyl-1-benzyl-3-[2-(ethoxycarbonyl)prop-2-enyl]-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043599Compound 14FEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100164 Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043600Compound 14GEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100163 Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043601Compound 14HEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

CSEARCH: UWLU-100167 Ethyl-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043602Compound 15AEur.J.Org.Chem., 2006, 2649-2660

Schematic spectra

Received
Accepted
Published

Publication
Corresponding Author

All Searches of the CAS-Registry File
were performed on 2018-02-26

Till Dec 15^th, 2005: Errors might happen - perfect error handling

Comparison of ¹³C-NMR Data

CSEARCH: UWLU-062227
Compound "Table 1 / Entry 1"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043579
Compound 9A
Eur.J.Org.Chem.,2006,2649-2660

CSEARCH: UWLU-062228
Compound "Table 1 / Entry 2"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043580
Compound 9B
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-062229
Compound "Table 1 / Entry 3"
Org.Lett., 7, 1117 - 1119 (2005)

8 aromatic lines expected; 4 given
Melting point: 167^oC

CSEARCH: UWLU-043581
Compound 9C
Eur.J.Org.Chem., 2006, 2649-2660

8 aromatic lines expected; 8 given
Melting point: 157^oC

CSEARCH: UWLU-062230
Compound "Table 1 / Entry 4"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043582
Compound 9D
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-062231
Compound "Table 1 / Entry 5"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043583
Compound 9E
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-062232
Compound "Table 1 / Entry 6"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043584
Compound 9F
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-062233
Compound "Table 1 / Entry 7"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043585
Compound 9G
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-062234
Compound "Table 1 / Entry 8"
Org.Lett., 7, 1117 - 1119 (2005)

CSEARCH: UWLU-043586
Compound 9H
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100153
ETHYL-4-ALLYL-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043587
Compound 13A
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100152
ETHYL-4-ALLYL-2,7-DIOXO-1-PHENYL-1,3-DIAZEPANE-4-CARBOXYLATE
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043588
Compound 13B
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100154
ETHYL-4-ALLYL-2,7-DIOXO-1-BENZYL-1,3-DIAZEPANE-4-CARBOXYLATE
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043589
Compound 13C
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100156
ETHYL-4-[2-CHLOROPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043590
Compound 13D
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100155
ETHYL-4-[2-METHYLPROP-2-ENYL]-2,7-DIOXO-1-PROPYL-1,3-DIAZEPANE-4-CARBOXYLATE
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043591
Compound 13E
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100157
Ethyl 3,4-diallyl-2,7-dioxo-1-propyl-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043594
Compound 14A
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100158
Ethyl 3,4-diallyl-2,7-dioxo-1-phenyl-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043595
Compound 14B
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100160
Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043596
Compound 14C
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100159
Ethyl 4-allyl-3-(2-methylprop-2-enyl)-1-phenyl-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043597
Compound 14D
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100162
Ethyl 4-allyl-1-benzyl-3-(2-chloroprop-2-enyl)-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043598
Compound 14E
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100161
Ethyl-4-allyl-1-benzyl-3-[2-(ethoxycarbonyl)prop-2-enyl]-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043599
Compound 14F
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100164
Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043600
Compound 14G
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100163
Ethyl 3-allyl-4-(2-chloroprop-2-enyl)-1-propyl-2,7-dioxo-1,3-diazepane-4-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043601
Compound 14H
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100167
Ethyl-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043602
Compound 15A
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100166
Ethyl-1,3-dioxo-2-phenyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043603
Compound 15B
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100171
Ethyl 2-benzyl-8-chloro-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043604
Compound 15C
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100165
Ethyl 8-methyl-1,3-dioxo-2-phenyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043605
Compound 15D
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100169
Ethyl 2-benzyl-8-(chloromethyl)-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)-carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-43606
Compound 15E
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100168
Diethyl 2-benzyl-1,3-dioxo-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a,8(1H)-dicarboxylate
Chem.Commun., 2005, 4477 - 4478

"Instead of the second generation Grubbs^TM catalyst, the second generation Hoveyda-Grubbs^TM catalyst was used for this reaction"
"Chromatography: first Hex/EtOAc (3/1) untill R_f = 0.26, then strip with EtOAc + 5% CH₂Cl₂"

CSEARCH: UWLU-043607
Compound 15F
Eur.J.Org.Chem., 2006, 2649-2660

"Instead of the second generation Grubbs^TM catalyst, the second generation Hoveyda-Grubbs^TM catalyst is used for this reaction"

"Chromatography: first Hex/EtOAc (3:1) until R_f = 0.26, then strip with EtOAc + 5 % CH₂Cl₂"

CSEARCH: UWLU-100172
Ethyl 7-chloro-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043608
Compound 15G
Eur.J.Org.Chem., 2006, 2649-2660

CSEARCH: UWLU-100170
Ethyl 7-methyl-1,3-dioxo-2-propyl-2,3,4,5,6,9-hexahydropyrido[1,2-c][1,3]diazepine-5a(1H)- carboxylate
Chem.Commun., 2005, 4477 - 4478

CSEARCH: UWLU-043609
Compound 15H
Eur.J.Org.Chem., 2006, 2649-2660

My Impression: A well hidden structure revision, but not good enough
to avoid detection by CSEARCH
Only detectable when the data of all 3 involved papers are electronically available

Feb 26^th, 2018

Feb 26^th, 2018

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Mar 8^th, 2018

FRI, Mar 9^th, 2018 / 10:25 (CET)

MON, Mar 12^th, 2018 / 16:03 (CET)

MON, Mar 12^th, 2018 / 16:36 (CET)

WED, Mar 14^th, 2018 / 17:59 (CET)