Abstract
Abstract With the aim of synthesizing novel functionalized derivatives of phosphinine (phosphabenzene), we investigated Diels-Alder approaches to 2-iodophosphinines. The precursor Cl2P-CHI2 reacted with triethylamine in the presence of 1,3-butadiene or its 2,3-dimethyl derivative to furnish 2-iodophosphinines 6 which, directly or after formation of their pentacarbonyltungsten complexes, underwent a number of interesting functionalization reactions. Useful for reaction with a number of electrophiles were the organozinc reagent 4,5-dimethyl-2-iodozincophosphinine (9) which could be obtained directly from the corresponding 2-iodophosphinine 6b and zinc either in DMF or in THF/TMEDA, and the pentacarbonyltungsten coordinated 2-lithio derivative 18.
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