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Abstract
The chemistry of pyramidal phospholes is governed by their low aromaticity and the strong σ,π overlap between the P-R exocyclic bond and the dienic system. Hence, functionalisation of the ring is difficult but [1,51 sigmatropic shift of R is easy. These two complementary aspects of phosphole chemistry are explored. Two routes to α-functional phospholes are described. They involve either a C-Br to C-Li exchange reaction or the allylic metallation of 3,4-dimethylphosphole-borane complexes. The influence of the atom connected to P (sp2C, spC, N, O, S) and the substitution pattern of the phosphole ring upon the [1,5] sigmatropic migration is discussed. Finally, several applications of this chemistry for the synthesis of water-soluble phosphines and polyphospha-macrocycles are described.