The stereoselective synthesis of cts-2-alkoxy-2-oxo-6-(iodomethyl)-l,2-oxaphosphorinanes is achieved by the treatment of , -dialkyl 4-pentenylphosphonates with iodine. The intermediates involved in iodine-induced cyclization reactions of ¿-unsaturated phosphonates could be observed directly by 31P NMR at 37 °C. The effects of the iodine concentration and solvents on the cyclization reaction were investigated. In chloroform, there were two intermediates, the major one being (4,5-diiodopentyl)phosphonate; the other one could be a cyclic alkyl trialkoxyphosphonium ion. In benzene and cyclohexane, in addition to these two intermediates, there was at
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