Evidence in favor of lithium-halogen exchange being faster than lithium-acidic hydrogen (deuterium) exchange

…, NM Sunder, R Ammanamanchi…

Index: Narasimhan, Nurani S.; Sunder, Nurani M.; Ammanamanchi, Radhakrishna; Bonde, Bhagavat D. Journal of the American Chemical Society, 1990 , vol. 112, # 11 p. 4431 - 4435

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Citation Number: 32

Abstract

Abstract: Treatment of 2-iodo-3-(deuterioxymethyl) quinoline with 1.5 equiv of n-butyllithium in ether, followed by aqueous work up, furnished 2-deuterio-3-(hydroxymethyl) quinoline in greater than 50% yield, confirming our earlier report,* which has been questioned by Beak and co-workers in this journal.'A mechanism is proposed, in which the reaction of n- butyllithium is faster with CI bond than with acidic deuterium. Further experiments are ...