S. Cai, W. Yin, Yuan Ma
Jan 1, 2007
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Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Mannich-type condensation of benzyl carbamate, aldehydes, and chlorophosphite has been widely used in the synthesis of 1-(N-benzyloxycarbonylamino)arylmethyl-phosphonic derivatives. Reactions of benzyl carbamate, aldehydes, and cyclic chlorophosphite 2-chloro-1,3,2-dioxaphospholane were conducted in benzene to afford a mixture of benzyl [(2-oxido-1,3,2-dioxaphospholane-2-yl)arylmethyl]-carbamates and 2-hydroxyethyl 1-(N-benzoxycarbonylamino)arylmethylphos-phonate monoesters. 2-hydroxyethyl 1-(N-benzoxycarbonylamino)arylmethylphos-phonate monoesters were obtained exclusively after the addition of water under stirring. The reaction mechanism was discussed. Their mass spectrometric fragmentations were also described.