Application of pertubation theory to free-radical benzylic and allylic oxidation of unconjugated π-systems

Gadi Rothenberg; Yoel Sasson

doi:10.1016/S0040-4020(98)01054-0

Application of pertubation theory to free-radical benzylic and allylic oxidation of unconjugated π-systems

Gadi Rothenberg, Yoel Sasson^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Pertubation interactions between Frontier Molecular Orbitals are utilized to predetermine the regioselectivity of allylic and benzylic oxidation reactions. Thus, it is shown that in unsaturated compounds containing two nonconjugated and nonequivalent n-systems, one system contributes mainly to the HOMO and the other to the HOMO-I. Analysis of four representative examples corroborates empirical evidence with previously published studies.

Original language	English
Pages (from-to)	561-568
Number of pages	8
Journal	Tetrahedron
Volume	55
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4020(98)01054-0
State	Published - 8 Jan 1999

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abstract = "Pertubation interactions between Frontier Molecular Orbitals are utilized to predetermine the regioselectivity of allylic and benzylic oxidation reactions. Thus, it is shown that in unsaturated compounds containing two nonconjugated and nonequivalent n-systems, one system contributes mainly to the HOMO and the other to the HOMO-I. Analysis of four representative examples corroborates empirical evidence with previously published studies.",

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AB - Pertubation interactions between Frontier Molecular Orbitals are utilized to predetermine the regioselectivity of allylic and benzylic oxidation reactions. Thus, it is shown that in unsaturated compounds containing two nonconjugated and nonequivalent n-systems, one system contributes mainly to the HOMO and the other to the HOMO-I. Analysis of four representative examples corroborates empirical evidence with previously published studies.

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Application of pertubation theory to free-radical benzylic and allylic oxidation of unconjugated π-systems

Abstract

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