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Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8155-8167

Rhodium(II)-catalyzed equilibration of push-pull carbonyl and ammonium ylides. A computationally based understanding of the reaction pathway

(6) Padwa, Albert a Snyder, James P a Curtis, Erin A a Sheehan, Scott M a Worsencroft, Kimberly J a Kappe, C Oliver b

a EMORY UNIVERSITY (United States)

b UNIVERSITY OF GRAZ (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0034734316 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja001088j Document Type: Article

Times cited : (92)

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83
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96
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- Although charge delocalization by resonance is an energy-lowering effect, this notation strictly applies to singly charged systems. Zwitterionic systems, supporting two oppositely charged centers, need to accommodate both charge delocalization and charge separation. The former stabilizes; the latter destabilizes.

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