Synthesis of P, As, Sb, and Bi Ylides (R1R2R3PCR4R5, etc.)

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Methods for the synthesis of phosphorus, arsenic, antimony, and bismuth ylides are reviewed for the period 1995–2003. The most frequently used method of synthesis for phosphorus ylides is via the salt method. A phosphonium salt is prepared, usually by the quarternization of a tertiary phosphine with an alkyl halide, which is then deprotonated, dehalogenated, or desilylated to form the ylide. Phosphorus ylides have also been prepared from phosphines. Most of the work in this area over this time period has focused on the reaction of an activated multiple bond with triphenylphosphine in the presence of a protic reagent. A wide range of ylides with extended carbon skeletons have been prepared in this manner. The preparation of phosphorus ylides from phosphines and carbenes as well as the preparation of more complex ylides from existing ylides is covered. The synthesis of As, Sb, and Bi ylides follows the same pattern as that for phosphorus ylides, although far less work has been done using these elements.