Issue 5, 2001
From the journal:

Chemical Communications

A novel oxime to pentathiepin cascade reaction

Sonia Macho,a   Charles W. Rees,*b   Teresa Rodrígueza  and  Tomás Torrobaa  

* Corresponding authors

a Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Burgos, Spain

b Department of Chemistry, Imperial College of Science, Technology and Medicine, London, UK
E-mail: c.rees@ic.ac.uk

Abstract

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.

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Article information

DOI
https://doi.org/10.1039/B100366F
Article type
Communication
Submitted
09 Jan 2001
Accepted
16 Jan 2001
First published
09 Feb 2001

Chem. Commun., 2001, 403-404

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A novel oxime to pentathiepin cascade reaction

S. Macho, C. W. Rees, T. Rodríguez and T. Torroba, Chem. Commun., 2001, 403 DOI: 10.1039/B100366F

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