Tetrahedron Letters

A convenient synthesis of thiirene 1-oxides

J Nakayama, K Takahashi, Y Sugihara, A Ishii

Index: Nakayama, Juzo; Takahashi, Kenta; Sugihara, Yoshiaki; Ishii, Akihiko Tetrahedron Letters, 2001 , vol. 42, # 24 p. 4017 - 4019

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Citation Number: 9

Abstract

Acetylenes (1), carrying two bulky alkyl substituents, reacted with sulfur dichloride (ClSCl) to give 2, 3-dialkyl-2, 3-dichlorothiiranes (2) nearly quantitatively. The alkaline hydrolysis of crude 2 resulted in the formation of thiirene 1-oxides (3) in 68–90% yields based on 1, thus providing a convenient synthesis of 3.

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Reactions of acetylenes, possessing bulky alkyl substituents, with S 2 Cl 2. Unexpected formation of α-oxothioketones, thiirene 1-oxides, and 1, 2-dithietes

[Nakayama; Takahashi; Watanabe; Sugihara; Ishii Tetrahedron Letters, 2000 , vol. 41, # 43 p. 8349 - 8352]

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