Synthèse de nouveaux phospholènes et phospholes avec substituants fonctionnels sur le phosphore

Abstract

1-Bromo-3,4-dimethyl-3-phospholene quaternizes readily with functional organic halides Z—(CH2)n—X with Z = OR, SR, C(O)R, CH(OR)2, COOR, CONR2, CN, n = 1 or 2, and X = Cl or Br. The adducts thus obtained are formally related to the diene-dihalophosphine McCormack cycloadducts. When reacting with H2O or H2S they yield the corresponding P-functional phospholene oxides or sulfides. Phospholes are also obtained by reaction with DBU when n = 1 and Z = OR, SR, or when n = 2 and Z = CN. Some chemical properties of these new compounds are described and pmr data are given.