Issue 18, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis and thermal transformation of stable monocyclic λ4-thiabenzenes

Hiroshi Shimizu,*a   Noriaki Kudo,a   Tadashi Kataokaa  and  Mikio Horia  

* Corresponding authors

a Gifu Pharmaceutical University, 5-6-1, Mitahora-higashi, Japan

Abstract

The stable monocyclic λ4-thiabenzenes 6a–e, which are stabilized with electron-withdrawing substituents such as benzoyl, cyano and alkoxycarbonyl groups, are synthesized in high yields by proton abstraction from the corresponding thiopyranium salts 5a–e with triethylamine in ethanol. The ylidic properties of the λ4-thiabenzenes are established based on spectral and chemical evidence. Thermal decomposition of the λ4-thiabenzenes affords alkyl-rearranged products 7, 8, and 9, thienofuran derivatives 10 (from benzoyl-substituted λ4-thiabenzenes), and thiophene derivatives 11. A plausible mechanism for the formation of those products is also discussed.

Graphical abstract: Synthesis and thermal transformation of stable monocyclic λ4-thiabenzenes

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Article information

DOI
https://doi.org/10.1039/B102806P
Article type
Paper
Submitted
27 Mar 2001
Accepted
11 Jul 2001
First published
24 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2269-2276

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Synthesis and thermal transformation of stable monocyclic λ4-thiabenzenes

H. Shimizu, N. Kudo, T. Kataoka and M. Hori, J. Chem. Soc., Perkin Trans. 1, 2001, 2269 DOI: 10.1039/B102806P

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