REACTIONS OF PHOSPHINE WITH 0.0(2,6).0(3,13).0(4,11).0(5,9)]-TETRADECAN-10-ONE DERIVATIVES

Iodoketone 2 reacts with triphenylphosphine or triethyl phosphite to f orm phosphonium salts 3 and 7 which fragment to an iodide 4 upon heati ng, The mechanism of C-C bond formation induced by phosphine and phosp hite is discussed, A 1,3,2-dioxaphospholane 8 was synthesized from dik etone 1 in two steps through an intermediate diol 10, although an atte mpt for a direct condensation of 1 and triphenylphosphine was unsucces sful, The reaction is rationalized with the aid of semi-empirical calc ulations, Crystal diffraction analyses for 3 and 8 are reported and so me of their bonding parameters are compared with the calculated values .