Sigmatropic isomerizations in azaallyl systems: XXII. 1, 3-proton transfer in (N-alkyltrifluoroacetimidoyl) phosphonates

PP Onys' ko, TV Kim, EI Kiseleva, YM Pustovit…

Index: Onys'ko; Kim; Kiseleva; Pustovit; Sinitsa Russian Journal of General Chemistry, 2005 , vol. 75, # 8 p. 1197 - 1203

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Citation Number: 12

Abstract

Abstract The reaction of N-alkyltrifluoroacetimidoyl chlorides with trialkyl phosphites leads to corresponding imidoylphosphonates CF 3 C [P (O)(OAlk) 2]= NCH 2 R. These compounds undergo irreversible 1, 3-H shift catalyzed by nitrogenous bases to give phosphorylated imines CF 3 CH [P (O)(OAlk) 2] N= CHR. The tendency for prototropism increases with increasing electronegativity of substituents R: CF 3> CH 2 OMe> H> Me. N-Cyclopentyl ...