Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin

Mahesh Pattabiraman; Arunkumar Natarajan; Lakshmi S. Kaanumalle; V. Ramamurthy

doi:10.1021/ol047866k

Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin

Mahesh Pattabiraman, Arunkumar Natarajan, Lakshmi S. Kaanumalle, V. Ramamurthy

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

172 Scopus citations

Abstract

(Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.

Original language	English (US)
Pages (from-to)	529-532
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	4
DOIs	https://doi.org/10.1021/ol047866k
State	Published - Feb 17 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.",

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AU - Pattabiraman, Mahesh

AU - Natarajan, Arunkumar

AU - Kaanumalle, Lakshmi S.

AU - Ramamurthy, V.

PY - 2005/2/17

Y1 - 2005/2/17

N2 - (Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.

AB - (Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.

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Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin

Abstract

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