Stereoelectronic effects in the hydrolysis of ethyl and methyl ethylene phosphates

K Taira, T Fanni, DG Gorenstein

文献索引：Taira, Kazunari; Fanni, Tahsin; Gorenstein, David G. Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4531 - 4536

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被引用次数: 37

摘要

Ethyl and methyl ethylene phosphates 1 are shown to hydrolyze with complete endocyclic cleavage between pH 8 and 15 to yield ethyl and methyl 2-hydroxyethyl phosphates 3, respectively. A much slower reaction involving recyclization of the methyl hydroxyethyl phosphate 3 to form ethylene phosphate 4, which undergoes rapid further hydrolysis to 2- hydroxyethyl phosphate 5, is conveniently monitored by 31P NMR. The strained cyclic ...