- Silyl Phosphites. 16. Mechanism of the Perkow Reaction and the Kukhtin-Ramirez Reaction. Elucidation by means of a New Type of Phosphoryl Rearrangements Utilizing Silyl Phosphites
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Reactions of α-lithiated diethyl α-benzylphosphonate (4) with benzoyl chloride and chloroiodomethane afforded benzoylated and chloromethylated products (1 and 2) corresponding to the 1:1 carbonyl adducts of diethyl trimethylsilyl phosphite with benzil and phenacyl chloride which were not obtained by the reactions between the phosphite and benzil or phenacyl chloride.Pyrolysis of 1 and 2 afforded 1,3,2-dioxaphosphole (6) and enol phosphate (8).On the other hand, treatment of 1 and 2 with tetrabutylammonium fluoride afforded benzoin phosphate (7)and 1,2-epoxy phosphonate (14), respectively, as the main products.These results are also discussed in connection with the mechanism of the Perkow reaction and the Kukhtin-Ramirez reaction.
- Sekine, Mitsuo,Nakajima, Masashi,Hata, Tsujiaki
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p. 4030 - 4034
(2007/10/02)
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