Relationship between the configurations of 2-phenyltetrahydrothiophenium 1-methylides and their rearrangement products

K. Fujiwara, Y. Maeda, N. Shirai, Y. Sato

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

trans-2-Phenyltetrahydrothiophenium 1-methylide (trans-3), which is generated by fluoride ion-induced desilylation of trans-2-phenyl-1-[(trimethylsilyl)methyl]tetrahydrothiophenium salt (trans-2), gave a mixture of 1,4,5,10a-tetrahydro-3H-2-benzothiocine (4) ([2,3]sigmatropic rearrangement product) and 4-methylsulfanyl-1-phenyl-1-butene (5) (Hofmann elimination product). Ylide trans-3 cannot undergo [2,3]sigmatropic rearrangement because the ylide-carbon is too far from the phenyl group, and trans-3 would instead isomerize to cis-3. In this paper, we discuss the mechanism of the isomerization of trans-3 to cis-3.

Original languageEnglish
Pages (from-to)7055-7058
Number of pages4
JournalJournal of Organic Chemistry
Volume65
Issue number21
DOIs
Publication statusPublished - 20-10-2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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