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22.1.1.1.7.4.1 Variation 1: Phosphorus(III)-Substituted Sulfonium Ylides

DOI: 10.1055/sos-SD-022-00003

Aggarwal, V. K.; Richardson, J.; Winn, C. L.Science of Synthesis, (20052249.

Since phosphonium salts bearing an additional strongly electron-withdrawing group are CH acidic species, they can be used to generate sulfonium ylides bearing an α-phosphonium substituent. The reaction of phosphonium ylides with the CoreyKim reagent 69 (generated in situ from dimethyl sulfide and N-chlorosuccinimide) at 0°C in dichloro­methane affords dimethylsulfonium (triphenylphosphonio)methylide chlorides 111 in good yield (Scheme 70).[‌143‌]

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