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Tetrahedron. 2010 Jun 19;66(26):4434-4440.

Synthesis and Reactivity Studies of α,α-Difluoromethylphosphinates.

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Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, U.S.A.


The preparation and reactivity of some α,α-difluorophosphinates is investigated. Alkylation of H-phosphinates with LiHMDS and ClCF(2)H gives the corresponding α,α-difluorophosphinates in good yield. Deprotonation of these reagents with alkyllithium or LDA is then studied. Subtle electronic effects translate into significant differences in the deprotonation/alkylation of the two "Ciba-Geigy reagents" (EtO)(2)CRP(O)(OEt)H (R = H, Me). On the other hand, attempted methylation of difluoromethyl-octyl-phosphinic acid butyl ester resulted in the exclusive alkylation of the octyl chain. Finally, reaction with carbonyl compounds results in the formation of 1,1-difluoro-2-phosphinoyl compounds.

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