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Studies on organophosphorous compounds: IX. C ‐Phosphorylation of compounds bearing an active methylene group
Author(s) -
ChengYe Yuan,
YiXiang Ding,
HaiYan Long,
ShuSen Li
Publication year - 1983
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19830010112
Subject(s) - chemistry , phosphorylation , methylene , carbanion , selectivity , chloride , medicinal chemistry , organic chemistry , stereochemistry , catalysis , biochemistry
The behaviour of carbanions of para‐substituted benzylcyanides and ambident enolates toward phosphorylation has been examined. In the former case the C ‐phosphorylation proceeded smoothly, while the ambident enolate ions derived either from β‐diketones or from β‐ketoesters gave exclusively regiospecific O‐phosphorylation products on reaction with diethyl phosphoryl chloride. The experimental results are well supported by reaction selectivity in terms of E qo / E C.OC / based on EHMO calculation.