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Synthesis 2000; 2000(10): 1454-1458
DOI: 10.1055/s-2000-7109
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Convenient Syntheses of Biologically Relevant Vinyl and Divinyl Phosphates by Selective Dealkylation of the Corresponding Phosphites

Nanjing Zhang* , John E. Casida
  • *Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, CA 94720-3112, USA
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Publication Date:
31 December 2000 (online)

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Reactions of diethyl vinyl phosphite and divinyl methyl phosphite with iodine produce exclusively dealkylated intermediates, the highly reactive vinyl and divinyl phosphoroiodidates, which can be used as efficient phosphorylation reagents to prepare a variety of vinyl and divinyl organophosphorus compounds. Examples are given for the ethyl vinyl and divinyl analogs of the potent diethyl phosphate anticholinesterase agents diazoxon, chlorpyrifos oxon and paraoxon.

vinyl phosphite - vinyl phosphate - phosphorylation - insecticide - iodine - phosphorus - dealkylation

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