The Unexpected Course of Several Arbuzov-Michaelis Reactions; An Example of the Nucleophilicity of the Phosphoryl Group1a

HJ Harwood, DW Grisley Jr

Index: Harwood,H.J.; Grisley,D.W. Journal of the American Chemical Society, 1960 , vol. 82, p. 423 - 426

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Citation Number: 32

Abstract

Results In connection with a study on the Arbuzov-Michaelis reaction, the reaction of dimethyl phenylphosphonite (I) with/3-bromoethyl acetate was investigated. Although methyl phenyl-@-acetoxyethy1)-phosphinate (11) was the expected product, it was formed in not greater than 570 yield. A n isomer,/3-acetoxyethyl phenyl-(methyl)-phosphinate (IV) was obtained in 60% yield instead. The structure of the unexpected ester was established by ...