167280-11-7Relevant articles and documents
THE REACTIONS OF N,N-DIMETHYLPHOSPHORAMIDIC DIFLUORIDE WITH TRANS-2-SUBSTITUTED CYCLOALKANOLS
Fokin, E. A.,Sadovnikov, S. V.,Sosnov, A. V.
, p. 57 - 64 (2007/10/02)
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.
