The Journal of Organic Chemistry

Oxygen vs carbon alkylation of ethyl acetoacetate

WJ Le Noble, HF Morris

Index: Le Noble,W.J.; Morris,H.F. Journal of Organic Chemistry, 1969 , vol. 34, p. 1969 - 1973

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Citation Number: 57

Abstract

In HMPA the 0 atom of the ambident anion may well be more accessible than in any other known medium. This is supported by the data shown in Table 11. The O/C ratio does not change as the cation is varied in size from Na+ to NBu*+, nor does a reagent such as tetraglyme have any effect; the smallest cation, Li+, depresses the ratio somewhat. Reutov6 found such a depression with both lithium and sodium with the use