Observational analysis reveals improved reactivity of HWE-type reagents in synthesizing allenyl esters using ketenes, indicating efficiency of phosphorus bonds.
Methyl 2-[bis(benzylthio)phosphoryl]acetate and its analogues have proven to be efficient Horner–Wadsworth–Emmons (HWE)-type reagents for synthesizing conjugated allenyl esters and their analogues through reactions with disubstituted ketenes using Grignard reagents. A series of HWE-type reagents containing the bis(benzylthio)phosphoryl group showed better reactivity than corresponding HWE reagents, where two phosphorus–sulfur bonds were substituted with phosphorus–oxygen bonds.
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Nakao et al. (2025) studied this question.
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