Selective Syntheses of Bis[1,2]dithiolo[1,4]thiazines and Bis[1,2]dithiolopyrroles from Hünig's Base

Selective Syntheses of Bis[1,2]dithiolo[1,4]thiazines and Bis[1,2]dithiolopyrroles from Hünig's Base Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 1998, Volume: 63, Number: 7, Pages: 2189-2196 Pages count : 8 DOI: 10.1021/jo971864e

Authors

Rees Charles W. ¹ , White Andrew J.P. ¹ , Williams David J. ¹ , Rakitin Oleg A. ² , Marcos Carlos F. ³ , Polo Cecilia ³ , Torroba Tomás ³

Affiliations

1	Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, United Kingdom
2	N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Leninsky Prospect, 47, 117913 Moscow, Russia
3	Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain

The reaction of N,N-diisopropylethylamine (Hünig's base) and disulfur dichloride in 1,2-dichloroethane, in the presence of DABCO, gives 4-ethylbis[1,2]dithiolo[5,4-b][4‘,5‘-e][1,4]thiazine-3,5-dithione (1), or, by addition of oxygen donors, the 3-oxo-5-thione 2 or 3,5-dione 3 derivatives are selectively obtained. When the first reaction is performed in boiling chlorobenzene, 4-ethylbis[1,2]dithiolo[4,5-b][5‘,4‘-d]pyrrole-3,5-dithione (4) is obtained by sulfur extrusion from 1, and in the presence of oxygen donors, the 3-oxo-5-thione 5 or 3,5-dione 6 derivatives are selectively obtained. Some interconversions of compounds 1−6 are described, and a coherent set of reaction pathways for the formation of all six products is proposed. X-ray diffraction shows that the new bis-dithiolothiazine ring system of 1−3 is folded out of planarity about the thiazine N−S vector, with the N-ethyl group folded back over the thiazine ring in a scorpion-like conformation. The new bis-dithiolopyrrole ring system of 4−6 is planar and extensively delocalized.

Rees C.W. , White A.J.P. , Williams D.J. , Rakitin O.A. , Marcos C.F. , Polo C. , Torroba T.
Selective Syntheses of Bis[1,2]dithiolo[1,4]thiazines and Bis[1,2]dithiolopyrroles from Hünig's Base
Journal of Organic Chemistry. 1998. V.63. N7. P.2189-2196. DOI: 10.1021/jo971864e WOS Scopus OpenAlex

Web of science:	WOS:000073136500027
Scopus:	2-s2.0-0001441401
OpenAlex:	W2950979634

DB	Citing
OpenAlex	55
Scopus	64
Web of science	57