The Reactions Of N,N-Dimethylphosphoramidic Difluoride with Trans-2-Substituted Cycloalkanols

Abstract

An interaction between N,N-dimethylphosphoramidic difluoride and cyclic alcohols containing hydroxyl, alkylamine and methylthiol groups in the trans-β position was performed. Trans-1-ethylcyclopentane-1,2-diol and trans-2-(N-alkylamino)cyclopentanols react with N,N-dimethylphosphoramidic 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 gives a salt of phosphorodifluoridic acid and the corresponding cyclic N,N,N',N'-tetraalkyl-1,2-diamine whereas trans-2-methylthiocyclopentanol is converted to a salt of phosphorodifluoridic acid and N,N-dimethyl-N-(2-methylthiocyclopentyl)amine.^∗∗ Some of described reactions appear to be applicable for the synthesis of various organic compounds, e.g. phosphorylated 2-N,N-dialkylaminocyclopentanethiols.

Key Words:

• N,N-dimethylphosphoramidic difluoride
• N,N-dimethylphosphoramidothioic difluoride
• phosphorodifluoridic acid
• phosphorylated dialkylaminocyclopentanethiol
• N,N-dialkylaminocycloalkanol
• N,N,N',N'-tetraalkyl-1,2-diamine