PHOSPHORYLATED N-PROPARGYLAMINES-SYNTHESIS AND REACTIONS

Reaction of N-propargylaminophosphites with methyl iodide or sulfuryl chloride leads to N-propargylaminophosphonates or N-propargylaminophosphates. In the interaction of N-propargylaminophosphites with methyl iodide in the presence of triethylamine hydrochloride three reactivities were noted: 1) cyclization affording azaphospholes; 2) Arbuzov-type reaction giving N-proprgylaminophosphonates and 3) addition of HCI to the triple bond leading to N-allylaminophosphonates. Treatment of N-propargylminophosphonates and -thiophosphates with HCl (gas) leads to phosphorylated N-propargylammonium salts, not to the formation of adducts.