Issue 15, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Azafulvenium methides: new extended dipolar systems

Oliver B. Sutcliffe,a   Richard C. Storr,*a   Thomas L. Gilchrista  and  Paul Rafferty†b  

* Corresponding authors

a Department of Chemistry, University of Liverpool, Liverpool, UK
E-mail: rcstorr@liv.ac.uk

b Department of Medicinal Chemistry, Knoll Ltd., Nottingham, UK

Abstract

The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo[1,2-c][1,3]thiazole 2,2-dioxide 20 (R = Me), 22 and 23 undergo sigmatropic [1,8]H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The analogous 1,2-diazafulvenium methide 36 has been intercepted in [8π + 2π] cycloadditions with electron-rich silylated acetylenes to give adducts 37–40. This behaviour is partially explained by Frontier MO theory.

Graphical abstract: Azafulvenium methides: new extended dipolar systems

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Article information

DOI
https://doi.org/10.1039/B103250J
Article type
Paper
Submitted
11 Apr 2001
Accepted
20 Jun 2001
First published
13 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1795-1806

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Azafulvenium methides: new extended dipolar systems

O. B. Sutcliffe, R. C. Storr, T. L. Gilchrist and P. Rafferty, J. Chem. Soc., Perkin Trans. 1, 2001, 1795 DOI: 10.1039/B103250J

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