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Mechanism of Decomposition of Quasiphosphonium Intermediates: Borderline SN1 Character of Alkyl-Oxygen Fission in sec-Alkyloxyphosphonium Salts

Hudson H., Qureshi A.

Polish Journal of Chemistry

2005

Vol. 79 / nr 3

473-480

alkyl diphenylphosphinites ROPPh2 (R = Et, Pri, Bus , and 3-pentyl) with iodomethane at room temperature. Phosphorus chemical shifts for the sec-alkoxy(methyl)diphenylphosphonium iodides (_P 68.6-68.7 ppm) are at slightly higher field than for ethoxy(methyl)diphenylphosphonium iodide (_P 72.4 ppm), in accord with higher electron density at phosphorus in the secondary alkyl sytems. Relative rates of decomposition in CDCl3 (Me > Et > Pri >> neopentyl) are in accord with SN2-type cleavage of the R-O bond but within the secondary alkyl series the relative rates (Pri