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 language | English |
|---|---|
| Pages (from-to) | 7055-7058 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 65 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - 20-10-2000 |
| Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Organic Chemistry
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