Bulletin of the Chemical Society of Japan p. 218 - 223 (1982)
Update date:2022-08-04
Topics: P-C Bond Cleavage C-C Bond Cleavage
Sekine, Mitsuo
Nakajima, Masashi
Hata, Tsujiaki
α-Lithiated diethyl α-(trimethylsilyloxy)benzylphosphonate underwent facile acylation with various acylating agents to afford the corresponding α-acylated products in good yields.On treatment with the α-acylated products with 1 M NaOH-EtOH (1:1, v/v) the P-C bond was cleaved with elimination of diethyl phosphate to give α-hydroxy ketones predominantly.On the other hand, when diethyl α-acyl-α-ethoxybenzylphosphonates were treated under the same conditions, they were rather stable and recovered.However, the prolonged alkaline treatment or the use of 4 M NaOH-EtOH (1:1 v/v) resulted in the C-C bond cleavage giving carboxylic acids and diethyl α-ethoxybenzylphosphonate in quantitative yields, respectively.The mechanisms of the above two reactions were proposed and discussed in connection with the Perkow reaction and related reactions.
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