(p-Toluenesulfonylmethylene)triphenylphosphorane

[5554-81-4] C26H23O2PS (MW 430.50) InChI = 1S/C26H23O2PS/c1-22-17-19-26(20-18-22)30(27,28)21-29(23-11-5-2-6-12-23,24-13-7-3-8-14-24)25-15-9-4-10-16-25/h2-21H,1H3 InChIKey = UDJLRPGUUHGFBI-UHFFFAOYSA-N (sulfonyl-stabilized phosphorane reagent used for Wittig alkenation reactions to give (E)-vinyl sulfones on reactions with aldehydes;1, 2 synthesis of (Z)-γ-keto-α, β-unsaturated sulfones with chromium alkoxycarbene complexes3) Alternative Name: tosylmethylenetriphenylphosphorane. Physical Data: mp 186–187 °C,4 IR,4 UV,4 1H NMR.5 Solubility: sol CHCl3(15 mg 1.0 mL−1), fairly sol benzene, THF, EtOH (5 mg, 1.0 mL−1); insol water. Form Supplied: white crystalline powder. Preparative Methods: generated by deprotonation of the triphenyl(p-toluenesulfonyl)methylphosphonium halide salts, which can be prepared by heating of bromomethyl p-tolyl sulfone and Triphenylphosphine4, 5 or by treatment of p-toluenesulfonyl fluoride with Methylenetriphenylphosphorane5 (eq 1). (1) Handling, Storage, and Precautions: there is no special handling required but storage at 5 °C in a sealed container and drying prior to use are recommended.