Methylenethioxophosphorane (thiophosphene) intermediates in the reactions of diphenylmethylphosphonamidothioic chlorides with amines. Differences between the elimination–addition mechanisms of nucleophilic substitution for PS and PO substrates
Abstract
In reactions with R2NH (R = Me or Et) in CHCl3 the PS substrate Ph2CHP(S)(NMe2)Cl differs markedly from its PO counterpart: the rate of substitution is increased much more by a 4-nitro substituent but is also more sensitive to the bulk of the