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DOI: 10.1039/A702258A (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2539-2544

Dialkyl phosphonates and tetraalkyl bis(phosphonate)s from the decomposition of quasi-phosphonium ylidic phosphonates in aqueous conditions

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D. Vaughan Griffiths, Khalku Karim and Jayne E. Harris

Abstract

The reaction of dimethyl benzoylphosphonates 1 (X = 2-halogen or 2-CF3O) with trialkyl phosphite leads to the formation of carbene intermediates 3 which are trapped by trialkyl phosphite to give the corresponding ylidic phosphonates 4. In acidic conditions these ylidic phosphonates decompose to give tetraalkyl phenylmethylene-1,1-bis(phosphonate)s 6 but in neutral or basic conditions they give mainly dimethyl benzylphosphonates and trialkyl phosphate. Factors influencing the mode of decomposition have been investigated.

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