title: Relationship between the configurations of 2-phenyltetrahydrothiophenium 1-methylides and their rearrangement products
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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan.
authors.initials: K
authors.lastname: Fujiwara
authors.initials: Y
authors.lastname: Maeda
authors.initials: N
authors.lastname: Shirai
authors.initials: Y
authors.lastname: Sato