Abstract
Reaction of dialkyl alkylphosphonates with SOCl2 in the presence of DMF, reported by Maier, can serve as a convenient route to simple monoalkyl alkylphosphonochloridates. However, when a substrate contains a (2-dialkylamino)ethyl group as one of the ester functions, the course of the reaction is determined by the nature of the N-alkyl groups. With the NMe2 group present, reaction with SOCl2 occurs at nitrogen, and no exchange of groups at phosphorus takes place. The NEt2 group, on the other hand, directs the reaction to phosphorus, and the Maier reaction of the exchange of one ester group OR for Cl proceeds in high yields. © 1996 John Wiley & Sons, Inc.
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