Mesylate derivatives of. alpha.-hydroxy phosphonates. Formation of carbocations adjacent to the diethyl phosphonate group

X Creary, CC Geiger, K Hilton

文献索引：Creary, Xavier; Geiger, Cristina C.; Hilton, Kathryn Journal of the American Chemical Society, 1983 , vol. 105, # 9 p. 2851 - 2858

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被引用次数: 59

摘要

Abstract: Mesylates 3-6 have been prepared and reacted in a variety of solvents. Product, rate, and solvent effect studies implicate carbocationic intermediates in these solvolyses despite the electron-withdrawing PO (OEt), group. Mesylate 3 gave exclusive substitution products. Optically active 3 gave racemic products on trifluoroacetolysis. a-Deuterium isotope effects were also in line with a cationic intermediate. Mesylate 4 gave some ...