Control of Regiochemistry in Photodimerization through Micellar Preorientational Effect: 2-Substituted Naphthalenes

V. Ramesh; V. Ramamurthy

doi:10.1021/jo00177a029

Control of Regiochemistry in Photodimerization through Micellar Preorientational Effect: 2-Substituted Naphthalenes

V. Ramesh, V. Ramamurthy

Research output: Contribution to journal › Article

28 Scopus citations

Abstract

Photodimerization of 2-substituted naphthalenes in organic solvents has been well explored. In contrast to their behavior in organic solvents, in anionic and cationic micellar media enhanced reactivity and pronounced regioselectivity are observed. Reactivity enhancement in micellar media is attributed to the local concentration effect. Enhanced reactivity in CTAC and DTAC compared to CTAB micelles is attributed to the counterion effect, and the regioselective photodimerization observed in anionic and cationic micelles leading exclusively to the cis dimer or the products derived therefrom is rationalized on the basis of the preorientational effect of micelles.

Original language	English (US)
Pages (from-to)	536-539
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	49
Issue number	3
DOIs	https://doi.org/10.1021/jo00177a029
State	Published - Feb 1984
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Ramesh, V., & Ramamurthy, V. (1984). Control of Regiochemistry in Photodimerization through Micellar Preorientational Effect: 2-Substituted Naphthalenes. Journal of Organic Chemistry, 49(3), 536-539. https://doi.org/10.1021/jo00177a029

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AB - Photodimerization of 2-substituted naphthalenes in organic solvents has been well explored. In contrast to their behavior in organic solvents, in anionic and cationic micellar media enhanced reactivity and pronounced regioselectivity are observed. Reactivity enhancement in micellar media is attributed to the local concentration effect. Enhanced reactivity in CTAC and DTAC compared to CTAB micelles is attributed to the counterion effect, and the regioselective photodimerization observed in anionic and cationic micelles leading exclusively to the cis dimer or the products derived therefrom is rationalized on the basis of the preorientational effect of micelles.

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