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

J Nakayama, K Takahashi, T Watanabe, Y Sugihara…

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

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Citation Number: 11

Abstract

The reaction of di-t-butylacetylene with S2Cl2, followed by purification with silica-gel column chromatography, gave 2, 2, 5, 5-tetramethyl-4-oxo-3-hexanethione (4a)(37%) and 2, 3-di-t- butylthiirene 1-oxide (5a)(10%), which were formed by hydrolysis of the initial product, 2, 3- di-t-butyl-2, 3-dichloroepisulfide (3a). The same work-up of the reaction mixture of di (1- adamantyl) acetylene with S2Cl2 provided 2-oxoethanethione (4b)(4–33%), thiirene 1- ...