THE REACTIONS OF N,N-DIMETHYLPHOSPHORAMIDIC DIFLUORIDE WITH TRANS-2-SUBSTITUTED CYCLOALKANOLS

An interaction between N,N-dimethylphosphoramidic difluoride and cycli c alcohols containing hydroxyl, alkylamine and methylthiol groups in t he trans-beta position was performed. Trans-1-ethylcyclopentane-1,2-di ol and trans-2-(N-alkylamino)cyclopentanols react with N,N-dimethylpho sphoramidic difluoride to yield 1-ethyl-6-oxabicyclo(3.1.0)hexane and 6-alkyl-6-azabicyclo(3.1.0)hexane, respectively. In the case of trans- 2-(N,N-dialkylamino)cyclopentanols and cyclohexanols, such reaction gi ves a salt of phosphorodifluoridic acid and the corresponding cyclic N ,N,N',N'-tetraalkyl-1,2-diamine whereas trans-2-methylthiocyclopentano l is converted to a salt of phosphorodifluoridic acid and N,N-dimethyl -N-(2-methylthiocyclopentyl)amine.* Some of described reactions appea r to be applicable for the synthesis of various organic compounds, e.g . phosphorylated 2-N,N-dialkylaminocyclopentanethiols.