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Issue 14, 1998
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Novel chemical behaviour of a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide

Abstract

1,3,4,5,6,11a-Hexahydro-7E-2-benzothionine 5, which is a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide 8, has been synthesized by reaction of 1-methyl-2-phenyltetrahydrothiopyranium triflate 3 with sodium amide in liquid ammonia or by the fluoride ion-induced desilylation of trans-2-phenyl-1-[(trimethylsilyl)methyl]tetrahydrothiopyranium perchlorate trans-7. Compound 5 is stable at room temperature and reverts to ylide 8 by ring-opening.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1998, 2181-2184
Article type
Paper

Novel chemical behaviour of a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide

S. Doi, N. Shirai and Y. Sato, J. Chem. Soc., Perkin Trans. 1, 1998, 2181
DOI: 10.1039/A802309C

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