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The Aromaticity of Pericyclic Reaction Transition States

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Henry S. Rzepa

Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 A2Z, United Kingdom

J. Chem. Educ., 2007, 84 (9), p 1535

DOI: 10.1021/ed084p1535

Publication Date (Web): September 1, 2007

Section:

History, Education, and Documentation

Abstract

An approach is presented that starts from two fundamental concepts in organic chemistry, chirality and aromaticity, and combines them into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hückel-aromatic and chiral Möbius-aromatic transition states. This is illustrated using an example that leads to apparent contradictions if treated using more conventional selection rules, but is readily understood in terms of the aromatic transition-state model.

Keywords (Audience):

First-Year Undergraduate / General

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Problem Solving / Decision Making

Keywords (Subject):

Alkanes / Cycloalkanes

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