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Abstract
A one-pot synthesis of new bis(polyfluoroalkyl)dialkylaminophosphoramidates (RF(CH2)2O)2P(O)NR2 (1–6) (RF = C6F13, NR2 = NC5H10 (1), NC4H8 (2), NEt2 (3); RF = C8F17, NR2 = NC5H10 (4), NC4H8 (5), NEt2 (6)) and polyfluoroalkyl bis(dialkylamino)phosphoramidates RF(CH2)2OP(O)(NR2)2 (9–14) (RF = C6F13, NR2 = NC5H10 (9), NC4H8 (10), NEt2 (11); RF = C8F17, NR2 = NC5H10 (12), NC4H8 (13), NEt2 (14)) was performed through phosphorylation of corresponding highly fluorinated alcohols with P(O)Cl3 in dry diethyl ether followed by aminolysis. However, the former phosphoramidates (1–6) and corresponding morpholinyl derivatives 7 and 8 were alternatively prepared in better yields from phosphoramidation reaction of bis(fluoroalkyl)phosphites with amines in the presence of I2 and H2O2 in dichloromethane. All these phosphoramidates were obtained in good yields and characterized by multinuclear (1H, 13C, 31P and 19F) NMR, IR spectroscopy and HRMS.
Graphical Abstract
