Space constrained stereoselective geometric isomerization of 1,2-diphenylcyclopropane and stilbenes in an aqueous medium

A. Mohan Raj; Gaurav Sharma; Rajeev Prabhakar; V. Ramamurthy

doi:10.1021/acs.orglett.9b01176

Space constrained stereoselective geometric isomerization of 1,2-diphenylcyclopropane and stilbenes in an aqueous medium

A. Mohan Raj, Gaurav Sharma, Rajeev Prabhakar, V. Ramamurthy

Chemistry

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

4 Scopus citations

Abstract

Confinement provided by the reaction space alters the photostationary state isomer distribution during the geometric isomerization of excited 1,2-diphenylcyclopropane and stilbenes. The selectivity in 1,2-diphenylcyclopropane is suggested to result from the supramolecular steric hindrance exerted by the medium for the rotational motion. The alteration in the selectivity between a dimethyl and n-propyl substituted stilbenes is attributed to the medium influence on the location of the transition state on the ground state surface.

Original language	English (US)
Pages (from-to)	5243-5247
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.9b01176
State	Published - Jul 5 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Space constrained stereoselective geometric isomerization of 1,2-diphenylcyclopropane and stilbenes in an aqueous medium",

abstract = "Confinement provided by the reaction space alters the photostationary state isomer distribution during the geometric isomerization of excited 1,2-diphenylcyclopropane and stilbenes. The selectivity in 1,2-diphenylcyclopropane is suggested to result from the supramolecular steric hindrance exerted by the medium for the rotational motion. The alteration in the selectivity between a dimethyl and n-propyl substituted stilbenes is attributed to the medium influence on the location of the transition state on the ground state surface.",

author = "Raj, {A. Mohan} and Gaurav Sharma and Rajeev Prabhakar and V. Ramamurthy",

note = "Funding Information: V.R. (CHE-1807729) and R.P. (CHE-1664926) thank the National Science Foundation for financial support. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b01176",

language = "English (US)",

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AU - Raj, A. Mohan

AU - Sharma, Gaurav

AU - Prabhakar, Rajeev

AU - Ramamurthy, V.

PY - 2019/7/5

Y1 - 2019/7/5

N2 - Confinement provided by the reaction space alters the photostationary state isomer distribution during the geometric isomerization of excited 1,2-diphenylcyclopropane and stilbenes. The selectivity in 1,2-diphenylcyclopropane is suggested to result from the supramolecular steric hindrance exerted by the medium for the rotational motion. The alteration in the selectivity between a dimethyl and n-propyl substituted stilbenes is attributed to the medium influence on the location of the transition state on the ground state surface.

AB - Confinement provided by the reaction space alters the photostationary state isomer distribution during the geometric isomerization of excited 1,2-diphenylcyclopropane and stilbenes. The selectivity in 1,2-diphenylcyclopropane is suggested to result from the supramolecular steric hindrance exerted by the medium for the rotational motion. The alteration in the selectivity between a dimethyl and n-propyl substituted stilbenes is attributed to the medium influence on the location of the transition state on the ground state surface.

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Space constrained stereoselective geometric isomerization of 1,2-diphenylcyclopropane and stilbenes in an aqueous medium

Abstract

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