Issue 9, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

Tim Creed,a   Rino Leardini,b   Hamish McNab,*a   Daniele Nanni,b   Iain S. Nicolsona  and  David Reeda  

* Corresponding authors

a Department of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh, UK

b Dipartimento di Chimica Organica ‘A Mangini’, Università di Bologna, Viale Risorgimento 4, Bologna, Italy

Abstract

Flash vacuum pyrolysis (FVP) of the oxime ethers 12–14 and of the sulfides 18–20 at 650 °C (10−2–10−3 Torr) gave products derived from the corresponding iminyl and thiophenoxyl radicals. In all cases, benz[d ]isothiazoles (e.g., 26) are formed as major products viaSHi mechanisms though the yields are greatest with the iminyl precursors. Alternative pathways observed from the thiophenoxyls in specific cases include the formation of the anilinobenzothiophene 36 and of dibenzothiophene 23, via an SHi process and a spirodienyl rearrangement, respectively. There is no evidence for significant interconversion of the iminyl and thiophenoxyl species.

Graphical abstract: Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

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Article information

DOI
https://doi.org/10.1039/B009844M
Article type
Paper
Submitted
06 Dec 2000
Accepted
27 Feb 2001
First published
12 Apr 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1079-1085

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Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals

T. Creed, R. Leardini, H. McNab, D. Nanni, I. S. Nicolson and D. Reed, J. Chem. Soc., Perkin Trans. 1, 2001, 1079 DOI: 10.1039/B009844M

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