Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol-2-ones with NaHS

Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol-2-ones with NaHS Full article

Journal

Letters in Organic Chemistry
ISSN: 1570-1786 , E-ISSN: 1875-6255

Output data

Year: 2011, Volume: 8, Number: 3, Pages: 193-197 Pages count : 5 DOI: 10.2174/157017811795038331

Tags

Benzodithiol; benzopentathiepine; benzotrithiole; pentathiepine; mechanism; trithiole

Authors

Khomenko Tatyana M. ¹ , Korchagina Dina V. ¹ , Komarova Nina I. ¹ , Volcho Konstantin P. ¹ , Salakhutdinov Nariman F. ¹

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev av., 9, 630090 Novosibirsk, Russian Federation

The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6-aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 >> F, Cl > CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.

Khomenko T.M. , Korchagina D.V. , Komarova N.I. , Volcho K.P. , Salakhutdinov N.F.
Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol-2-ones with NaHS
Letters in Organic Chemistry. 2011. V.8. N3. P.193-197. DOI: 10.2174/157017811795038331 WOS Scopus РИНЦ

Published print:

Mar 1, 2011

Web of science	WOS:000288985000008
Scopus	2-s2.0-79953305118
Elibrary	16997628
OpenAlex	W2951313125