Abstract
Abstract The reaction of a dialkyl methylphosphonite with an alkyl N-chloroacetimide leads to the formation of the expected Arbusov reaction product (3) plus a dialkyl methylphosphonate and acetonitrile. For dissimilarly substituted reagents, a mixture of symmetrical (4) and unsymmetrical (5) dialkyl methylphos-phonates are produced. We have shown that the latter (4 and 5) result from a phosphonium intermediate (6), formed from an initial attack by phosphorus on the chlorine atom of the acetimide, followed by ligand exchange with alkoxide, and not from a simple air oxidation of the dialkyl methylphosphonite starting material. However, it is uncertain whether the Arbusov product is also formed via the same initial phosphonium intermediate (6), or whether competing paths of attack by tervalent phosphorus on the halogen vs. the nitrogen atom of the N-chloroacetimide are operative in this system.
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