NDLI: Photoreactions of substituted o-cresyl acylates in cyclohexane and in polyethylene films. The influences of intra- and inter-molecular ‘crowding’ effects

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Photoreactions of substituted o-cresyl acylates in cyclohexane and in polyethylene films. The influences of intra- and inter-molecular ‘crowding’ effects

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Photochemical & Photobiological Sciences Vol - 8 Issue - 6

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Photoreactions of substituted o-cresyl acylates in cyclohexane and in polyethylene films. The influences of intra- and inter-molecular ‘crowding’ effects

Content Provider	Royal Society of Chemistry (RSC)
Author	Chen, Yu-Zhe Weiss, Richard G.
Copyright Year	2009
Abstract	Photo-Fries rearrangements and associated photoreactions of four o-cresyl acylates were investigated in cyclohexane and in unstretched and stretched polyethylene (PE) films with different degrees of crystallinity. The esters differ in the number of phenyl substituents attached to the methyl group of the cresyl part and the length of the acyl chain. The influences of intramolecular structural factors and intermolecular environmental effects on the fates of the excited singlet states and the singlet state aryloxy/acyl radical pairs generated subsequently from them are explored. The results indicate that there are definable limits to the selectivity of the photoreactions of aryl esters that are dependent on their shapes and the ability of their environments to interact with them. Quantum yields for the reactions of the o-cresyl acylates were measured in cyclohexane and their values can be understood on the bases of a combination of conformational and electronic factors. The PE cavities holding the less globularly shaped o-cresyl acylates act as templates for the formation of the photoproducts: the ratios of the 2- and 4-position photo-Fries rearrangement products from o-cresyl acetate and 2-benzylphenyl acetate are higher when irradiated in films that are stretched or have higher film crystallinity; control by the PE cavities over the fates of the radical pairs is diminished for the o-cresyl acylate with two phenyl groups appended to the methyl of the cresyl part. The cavities of the PE films exert an interesting influence on the ability of the excited singlet states to undergo concerted decarboxylation reactions as well.
Starting Page	916
Ending Page	925
Page Count	10
File Format	HTM / HTML PDF
ISSN	1474905X
Volume Number	8
Issue Number	7
Journal	Photochemical & Photobiological Sciences
DOI	10.1039/b902109d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Polyethylene Aromaticity Methyl group Interaction Decarboxylation Cyclohexane Phenyl group Fries rearrangement Pyrimidine dimer
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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Pyrimidine reactions. Part XX. Thermal rearrangement of 5-(p-substituted phenyl)-2(and 4)-methoxypyrimidines

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Reactions of methyl radicals with cyclohexane and methyl-substituted cyclohexanes

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Photoreactions of substituted o-cresyl acylates in cyclohexane and in polyethylene films. The influences of intra- and inter-molecular ‘crowding’ effects

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