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Abstract
1,2,3-diazaphospholines of new type containing an enamine residue, conjugated with the diazaphospholine cycle, were synthesized by phosphorylation of N,N-dimethyl- and N-substituted hydrazones of ω-fomyl-1,3,3-trimethyl-2-methyleneindolines using phosphorus(III) halides. Reversible ionization of the P-Br bond was observed for a 2-N-methyl-3-P-bromodiazaphospholine in polar solvents. The ionization is caused by stabilization of the phosphenium ion by electrondonating methyl and enamine group. Analogously, 2-N-phenyl-3-P-bromo- as well as 3-P-chloro-1,2,3-diazaphospholines give stable phosphenium ions only after treatment of sodium tetraphenylborate or trimethylsilyl trifluoromethanesulfonate.