Journal of Organic Chemistry p. 5349 - 5356 (1987)
Update date:2022-09-26
Topics:
Galli, Remo
Reaction between (α-haloalkyl)phosphonium salts and some sulfur nucleophiles leads to the substitution product Ph3P+CH2SRX-.Evidence is presented that this substitution is not a normal SN2 reaction and that it occurs through formation of a phosphonium ylide and a disulfide, reaction between them, and action of the resulting salt on the starting phosphonium salt.Then RSX and Ph3=CH2 reenter the sequence, giving rise to a three-step chain nucleophilic substitution.
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Doi:10.1021/jo802391x
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(1987)
