[1,3,4]THIAZAPHOSPHOLIDINE .4. [1,3,4]THI AZAPHOSPHOLIDINSULFIDE AND [1,3,4]THIAZAPHOSPHOLIDINOXIDE ETHINYLAMINOPHOSPHANES

The synthesis of the ethinylaminophosphanes 1-5 from substituted alkin ylmagnesium bromides and halogenoaminophosphanes is described. Reactio n of 1 with various derivatives of urea yields the [1,3,4]thiazaphosph olidines 6, 7, 11-13. 2 reacts with thiouracil to give compound 15, wi th 2-mercaptobenzimidazole to give compound 16 and 3 reacts with 2-mer captobenzimidazole to give compound 17. The new [1,3,4]thiazaphospholi dines can be transferred into the corresponding sulfides by heating wi th elemental sulfur or into their oxides by treatment with t-butyl-hyd roperoxide. The spirocyclic compound 31 is the product from the reacti on of 13 with o-chloranil. All new ethinylaminophosphanes, [1,3,4]thia zaphospholidines and their sulfides and oxides are characterized by nm r, mass and ir spectra. X-ray structure analyses of 15, 21 and 26 were performed.