Journal of Organic Chemistry p. 54 - 57 (1983)
Update date:2022-08-29
Topics:
Takaki, Ken
Yasumura, Masateru
Negoro, Kenji
Dimethyl selenide reacts with N-chlorosuccinimide (NCS) to give a new complex, with which various alcohols are successfully oxidized to carbonyl compounds.Notably, this method is applicable to allylic alcohols without formation of allylic chlorides and rearranged products. β-Hydroxy selenide 8 is converted to β-oxo selenide 9 by treatment with NCS.On the other hand, facile deselenization occurs in the case of γ-hydroxy selenide 10 under similar conditions.A plausible mechanism of the reactions is also discussed.
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