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Type I and type II photochemical reaction of ω-isobutyryl-ω-methyl-2,3-benzocycloalk-2-en-1-ones by Michikazu Yoshioka; Masahiro Saitosh; Hideaki Arai; Keiji Ichikawa; Tadashi Hasegawa is a Chemistry article available to read on EtoBox.

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w-Isobutyryl-w-methyl-2.3-benzocycloalk-2-en-l-ones (6a-cl undergo both type I and type II photoreactions. The type I/type II product ratio depends on the ring size; the six-membered ketone 6a is subject to type II reaction and the eight-membered ketone 6~ is subject to type I reaction predominantly. The cyclization/elimination ratio of the type II reaction of 6 also depends on the ring size; the ratio decreases with increasing ring size. The two major photochemical processes of ketones, Norrish type I and Norrish type II, have been widely studied.' The ketones with r-hydrogens and a-substituents In the alkyl chain undergo competitive type I and type II reactions. 2 The cyclic ketones with r-hydrogens also undergo both reactions. 3 The reactivity of the type II reaction increases with decreasing rC-H bond strength and decreases with the electron-withdrawing groups on Y carbon. 4 The reactivity of the type I reaction increases with a substituents. 2 In the case of aliphatic 1,3-diketones, no example of type II reaction where an a-hydrogen to one carbonyl group undergoes 1,5-shift to another carbonyl oxygen has been found. The non-enolizable aliphatic 1,3-diketones undergo type I rea

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Author

Michikazu Yoshioka; Masahiro Saitosh; Hideaki Arai; Keiji Ichikawa; Tadashi Hasegawa

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1987

Language

EN

Field

Chemistry (Physical Sciences)