1,1-Diphenylalkenes. Part II. Alkylation of 1,1-diphenylpropene carbanions. The principle of least motion
Abstract
Carbanions of the type [Ph2C
CH
CHR]– were alkylated in liquid ammonia. A preponderance of α-alkylation occurred when R was H or Me, in accord with the principle of least motion. Contrary to predictions, exclusive α-alkylation occurred when R was Ph. The mechanism and synthetic utility of these reactions are discussed.
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