Journal of the Chemical Society. Perkin Transactions 2 (2001) p. 2681 - 2685 (1996)
Update date:2022-08-29
Topics:
Chow, Tahsin J.
Li, Lih-Pyng
Lee, Vincent Y. R.
Lin, Kuan-Jiuh
Chen, Chong-Yow
Iodoketone 2 reacts with triphenylphosphine or triethyl phosphite to form phosphonium salts 3 and 7 which fragment to an iodide 4 upon heating. The mechanism of C-C bond formation induced by phosphine and phosphite is discussed. A 1,3,2-dioxaphospholane 8 was synthesized from diketone 1 in two steps through an intermediate diol 10, although an attempt for a direct condensation of 1 and triphenylphosphine was unsuccessful. The reaction is rationalized with the aid of semi-empirical calculations. Crystal diffraction analyses for 3 and 8 are reported and some of their bonding parameters are compared with the calculated values.
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