TY - JOUR
T1 - Relationship between the configurations of 2-phenyltetrahydrothiophenium 1-methylides and their rearrangement products
AU - Fujiwara, K.
AU - Maeda, Y.
AU - Shirai, N.
AU - Sato, Y.
PY - 2000/10/20
Y1 - 2000/10/20
N2 - 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.
AB - 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.
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U2 - 10.1021/jo0007377
DO - 10.1021/jo0007377
M3 - Article
AN - SCOPUS:0034693305
SN - 0022-3263
VL - 65
SP - 7055
EP - 7058
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -