Preparative Organic Chemistry
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ChemInform Abstract: Evidence in Favor of Lithium-Halogen Exchange Being Faster Than Lithium-Acidic Hydrogen (Deuterium) Exchange.
First published: September 11, 1990
Abstract
Reaction of the iodo(deuterio-oxymethyl)quinoline (I) with BuLi (II) affords the 2-deuterioquinoline (III) with > 50% yield, confirming earlier reports which are questioned by other workers.
ChemInform Abstract
Reaction of the iodo(deuterio-oxymethyl)quinoline (I) with BuLi (II) affords the 2-deuterioquinoline (III) with > 50% yield, confirming earlier reports which are questioned by other workers. A mechanism is suggested, in which the reaction of BuLi with the C-I bond is faster than with the acidic deuterium. It is possible that this is caused by the radical nature of this reaction.
