What question did this study set out to answer?

To examine the reaction mechanisms and rearrangement pathways of benzyl-type quaternary ammonium salts when treated with various organolithium bases.

April 1, 1967The Journal of Organic Chemistry

Rearrangements and other reactions of benzyl-type-quaternary ammonium ions with certain organolithium reagents

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Authors

KKKarl P. Klein DEDonald N. Van Eenam CHCharles R. HauserCentre National de la Recherche Scientifique

Discussion

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Implication

Experimental study demonstrates rearrangement pathways in benzyl quaternary ammonium ions treated with organolithium reagents, highlighting reactive ylide intermediates.

Key Points

To examine the reaction mechanisms and rearrangement pathways of benzyl-type quaternary ammonium salts when treated with various organolithium bases.
Treated benzyl-type quaternary ammonium ions with selected organolithium reagents in anhydrous organic media.
Isolated and characterized the resulting rearrangement products, fragmentation products, and tertiary amine derivatives.
Organolithium reagents deprotonated the quaternary ammonium salts to form reactive ammonium ylides that underwent characteristic molecular rearrangements.
Identified competitive reaction pathways, including benzylic rearrangements and nucleophilic displacement, governed by the structure of the ammonium substrate and base.

Cite This Study

Klein et al. (1967) studied this question.

synapsesocial.com/papers/6aa69b39014c9b816df4f674 https://doi.org/10.1021/jo01279a066

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Implication

Experimental study demonstrates rearrangement pathways in benzyl quaternary ammonium ions treated with organolithium reagents, highlighting reactive ylide intermediates.

Rearrangements and other reactions of benzyl-type-quaternary ammonium ions with certain organolithium reagents

Discussion

Member takes

Implication

Key Points

Cite This Study

Rearrangements and other reactions of benzyl-type-quaternary ammonium ions with certain organolithium reagents

Discussion

Member takes

Implication

Key Points

Cite This Study

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