[1,3,4]Thiazaphospholidine IV^†; [1,3,4]Thiazaphospholidinsulfide und -Oxide, Ethinylaminophosphane

Abstract

The synthesis of the ethinylaminophosphanes 1-5 from substituted alkinylmagnesium bromides and halogenoaminophosphanes is described. Reaction of 1 with various derivatives of urea yields the [1,3,4]thiazaphospholidines 6, 7, 11-13. 2 reacts with thiouracil to give compound 15, with 2-mercapto-benzimidazole to give compound 16 and 3 reacts with 2-mercaptobenzimidazole to give compound 17. The new [1,3,4]thiazaphospholidines can be transferred into the corresponding sulfides by heating with elemental sulfur or into their oxides by treatment with t-butyl-hydroperoxide. The spirocyclic compound 31 is the product from the reaction of 13 with o-chloranil. All new ethinylaminophosphanes, [1,3,4]thiazaphospholidines and their sulfides and oxides are characterized by nmr, mass and ir spectra. X-ray structure analyses of 15, 21 and 26 were performed.

Key Words:

• Ethinylaminophosphanes
• [1,3,4]thiazaphospholidines
• [1,3,4]thiazaphospholidine sulfides
• [1,3,4]thiazaphospholidine oxides
• nmr
• mass spectra
• X-ray crystal structures