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Thiosulfonium ions. Methylthiolation of 3-methylthio-1-butene and cis- and trans-1-methylthio-2-butene

✍ Scribed by Jhong K. Kim; Marjorie C. Caserio

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 277 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82092-x

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✦ Synopsis

Whereas sulfenyl reagents commonly add to carbon double bonds, addition to sulfur of 3-methylthio-1-butene precedes attack at carbon to give allylic thiosulfonium ions that form reversibly and which rearrange rapidly to trans-2-butenyl analogs.

Likewise, rearrangement of cis-to trans-1-methylthio-2-butene occurs by way of thiosulfonium ions.

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