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The redox behaviour of sterically constrained tricyclic phosphine 3a was investigated by spectroelectrochemistry. The data suggested a highly negative reduction potential with the reversible formation of a dianionic species. Accordingly, 3a reacted with two equivalents of Li/naphthalene by reductive cleavage of a P-C bond of one of the PC 4 heterocycles. The resulting dilithium compound 5 represents a phosphaindole derivative with annulated aromatic C 6 and PC 4 rings. It is an interesting starting material for the synthesis of new heterocyclic molecules, as was shown by treatment with Me 2 SiCl 2 and PhPCl 2 . The structures of the products ( 6 and 7 ) formally reflect ring expansion by insertion of silylen or phosphinidene fragments into a P-C bond of 3a . Treatment of 3a with H 2 O 2 did not result in the usually observed transfer of a single O atom to phosphorus, but oxidative cleavage of a strained PC 4 ring afforded a bicyclic phosphinic acid, R 2 PO 2 H.

chemical science

Sterically constrained tricyclic phosphine: redox behaviour, reductive and oxidative cleavage of P–C bonds, generation of a dilithium phosphaindole as a promising synthon in phosphine chemistry