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Photochemistry of large ring 2-phenylcycloalkanone in the presence of molecular oxygen

Paper ID Volume ID Publish Year Pages File Format Full-Text
28362 44071 2007 8 PDF Available
Title
Photochemistry of large ring 2-phenylcycloalkanone in the presence of molecular oxygen
Abstract

Photolysis of 2-phenylcyclododecanone (2PCDD, ring size: C12) has been investigated in an air-saturated solution. The α-photocleavage of 2PCDD (Norrish type I) has led to the formation of triplet acyl-benzyl biradical (3BR) which reacts with O2 to produce a peroxyester intermediate. A major photoproduct of 2-phenyl-1-oxacyclododecane is formed by a stepwise decarboxylation from the peroxyester intermediate. The peroxyester is also a common intermediate for minor products of benzaldehyde, cyclodecane, and acetophenone. 1-Phenylcycloundecane is produced from decarbonylation of 3BR. On the other hand, 3BR undergoes intersystem crossing to the singlet biradical which in turn recombines to form the parent 2PCDD or to afford a cage product of cyclophane. The recombination yield to the starting species is estimated to be 0.5 by measuring a time evolution of enantiomer concentration of 2PCDD starting from one optically pure enantiomer. Photolysis mechanism of 2PCDD in the presence of molecular oxygen has been proposed and discussed.

Keywords
Cyclic ketone; Norrish type I photolysis; Biradical; Photooxidation; Molecular oxygen
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Photochemistry of large ring 2-phenylcycloalkanone in the presence of molecular oxygen
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 186, Issues 2–3, 25 February 2007, Pages 290–297
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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