A novel oxime to pentathiepin cascade reaction

An extensive domino sequence, including a vinylogous sulfur-assisted Beckmann fragmentation, is involved in the one-pot conversion of a dioxime 3 by S2Cl2 into a cyanoethyl-1,2,3-dithiazole 5 and a novel tricyclic pentathiepin 6; the yield of 6 is increased by added lithium sulfide, and both 5 and 6...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) no. 5; pp. 403 - 404
Main Authors Macho, S, Rees, CW, Rodriguez, T, Torroba, T
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2001
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
BENZOPENTATHIEPINS
VARACIN
Online AccessGet full text

Cover

More Information
Summary:An extensive domino sequence, including a vinylogous sulfur-assisted Beckmann fragmentation, is involved in the one-pot conversion of a dioxime 3 by S2Cl2 into a cyanoethyl-1,2,3-dithiazole 5 and a novel tricyclic pentathiepin 6; the yield of 6 is increased by added lithium sulfide, and both 5 and 6 are formed in higher yield from 2-(cyanoethyl)cyclopentanone oxime 7; reaction mechanisms are proposed for these cascade reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/b100366f