Inter- and Intramolecular Photocycloaddition of Aromatic Compounds

Authored by: Hajime Maeda , Kazuhiko Mizuno

CRC Handbook of Organic Photochemistry and Photobiology

Print publication date:  March  2012
Online publication date:  March  2012

Print ISBN: 9781439899335
eBook ISBN: 9781466561250
Adobe ISBN:

10.1201/b12252-21

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Abstract

Photocycloaddition of alkenes to aromatic rings is an important method for chemical conversion and construction of polycyclic compounds. In comparison with photocycloaddition of two alkenes and that of enone with alkenes, mild and chemoselective excitation by light is possible because aromatic rings often have absorption bands in longer wavelengths. In addition, most of them proceed via structurally controlled exciplexes consisting of aromatic rings with alkenes. 1 Therefore, highly selective photocyclo-addition can be designed by control of structure and reactivity of substrates and exciplexes, although there are several modes in photocycloaddition of aromatic rings with alkenes, these are [2 + 2], [3 + 2], [4 + 2], [4 + 4], and so on.

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