Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia

Carl L. Bumgardner; Hon Bin Hsu; F. Afghahi; William L. Roberts; Suzanne T. Purrington

doi:10.1021/jo01328a003

Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia

Carl L. Bumgardner, Hon Bin Hsu, F. Afghahi, William L. Roberts, Suzanne T. Purrington

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14 Scopus citations

Abstract

Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned.

Original language	English (US)
Pages (from-to)	2348-2353
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	44
Issue number	14
DOIs	https://doi.org/10.1021/jo01328a003
State	Published - Feb 1 1979
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia",

abstract = "Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned.",

author = "Bumgardner, {Carl L.} and Hsu, {Hon Bin} and F. Afghahi and Roberts, {William L.} and Purrington, {Suzanne T.}",

year = "1979",

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T1 - Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia

AU - Bumgardner, Carl L.

AU - Hsu, Hon Bin

AU - Afghahi, F.

AU - Roberts, William L.

AU - Purrington, Suzanne T.

PY - 1979/2/1

Y1 - 1979/2/1

N2 - Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned.

AB - Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned.

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U2 - 10.1021/jo01328a003

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Reactions of Alkylbenzyldimethylammonium Halides with Amide in Liquid Ammonia

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