Journal of Organic Chemistry p. 716 - 719 (1988)
Update date:2022-07-29
Topics:
Zhang, Jian-Jian
Schuster, Gary B.
The direct irradiation of 9-dimethylsulfonium fluorenylide (DMSF) in acetonitrile or THF gives primarily the Stevens rearrangement product 9-methyl-9-(methylthio)fluorene and the dimeric bis<9-(methylthio)fluorenyl>.The mechanism of this reaction was investigated by kinetic, product, and isotope tracer techniques.The results indicate that the primary photochemical step is bond homolysis from an n?* singlet state of the ylide.Oxidation of the ylide does not lead to chemical reaction.
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