Journal of Organic Chemistry p. 4030 - 4034 (1981)
Update date:2022-07-30
Topics:
Sekine, Mitsuo
Nakajima, Masashi
Hata, Tsujiaki
Reactions of α-lithiated diethyl α-<(trimethylsilyl)oxy>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.
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Doi:10.1055/s-2007-985567
(2007)Doi:10.1016/0040-4039(91)80223-S
(1991)Doi:10.1055/s-2000-8235
(2000)Doi:10.1055/s-1981-29487
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(2002)Doi:10.1016/S0040-4039(01)90476-9
(1981)