Modification of photochemical reactivity by cyclodextrin complexation: Consequences of restricted rotation of Norrish type II 1,4-diradicals from aryl alkyl ketones

G. Dasaratha Reddy, B. Jayasree, Vaidhyanathan Ramamurthy

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Abstract

Photochemical behavior of aryl alkyl ketones complexed to β-cyclodextrin both in aqueous solution and in the solid state have been investigated. Comparison of the above behavior with that in isotropic solvents reveals that cyclodextrin inclusion provides an environment wherein photoreactions may be carried out with consequences different from those observed in homogeneous solution. Products of elimination and cyclization resulting from the Norrish type II hydrogen abstraction were monitored. The ratio of these products was dependent on the length but not on the bulkiness of the alkyl substituent. These observations are rationalized on the basis of the steric constraints by the cyclodextrin cavity on the rotational motions of the 1,4-diradical.

Original languageEnglish
Pages (from-to)3107-3113
Number of pages7
JournalJournal of Organic Chemistry
Volume52
Issue number14
StatePublished - Dec 1 1987
Externally publishedYes

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Cyclodextrins
Ketones
Complexation
Cyclization
Hydrogen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Photochemical behavior of aryl alkyl ketones complexed to β-cyclodextrin both in aqueous solution and in the solid state have been investigated. Comparison of the above behavior with that in isotropic solvents reveals that cyclodextrin inclusion provides an environment wherein photoreactions may be carried out with consequences different from those observed in homogeneous solution. Products of elimination and cyclization resulting from the Norrish type II hydrogen abstraction were monitored. The ratio of these products was dependent on the length but not on the bulkiness of the alkyl substituent. These observations are rationalized on the basis of the steric constraints by the cyclodextrin cavity on the rotational motions of the 1,4-diradical.",
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T1 - Modification of photochemical reactivity by cyclodextrin complexation

T2 - Consequences of restricted rotation of Norrish type II 1,4-diradicals from aryl alkyl ketones

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AU - Jayasree, B.

AU - Ramamurthy, Vaidhyanathan

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Y1 - 1987/12/1

N2 - Photochemical behavior of aryl alkyl ketones complexed to β-cyclodextrin both in aqueous solution and in the solid state have been investigated. Comparison of the above behavior with that in isotropic solvents reveals that cyclodextrin inclusion provides an environment wherein photoreactions may be carried out with consequences different from those observed in homogeneous solution. Products of elimination and cyclization resulting from the Norrish type II hydrogen abstraction were monitored. The ratio of these products was dependent on the length but not on the bulkiness of the alkyl substituent. These observations are rationalized on the basis of the steric constraints by the cyclodextrin cavity on the rotational motions of the 1,4-diradical.

AB - Photochemical behavior of aryl alkyl ketones complexed to β-cyclodextrin both in aqueous solution and in the solid state have been investigated. Comparison of the above behavior with that in isotropic solvents reveals that cyclodextrin inclusion provides an environment wherein photoreactions may be carried out with consequences different from those observed in homogeneous solution. Products of elimination and cyclization resulting from the Norrish type II hydrogen abstraction were monitored. The ratio of these products was dependent on the length but not on the bulkiness of the alkyl substituent. These observations are rationalized on the basis of the steric constraints by the cyclodextrin cavity on the rotational motions of the 1,4-diradical.

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