Abstract
Abstract The interaction of diphenyl phosphorochloridate and three dialkyl phosphorochloridates (alkyl = Et, Me, Bzl) with pyridine was shown by 31P NMR spectroscopy to lead to the formation of a diorganyl phosphoropyridinium intermediate. In the case of diethyl, dimethyl and dibenzyl phosphorochloridate, 31P NMR spectroscopy studies showed that their decomposition in pyridine solution resulted from pyridine-mediated dealkylation of the dialkyl phosphoropyridinium intermediate followed by the generation of diphosphate and triphosphate species. The use of the sterically hindered bases, 2-methyl-pyridine and 2,6-dimethylpyridine, showed that increased steric hindrance of the tertiary base caused a significant reduction in the extent of decomposition of the dialkyl phosphoro-N-pyridinium intermediate.
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