Photooxygenation, [2+2] and [4+2]

Authored by: Maria Rosaria Iesce , Flavio Cermola

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/b12252-31

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Abstract

The great synthetic potential of peroxides accounts for the wide interest of scientific community to the photooxygenation reaction that represents one of the most versatile and simple procedures to prepare a variety of peroxides. Generally the reaction is carried out in the presence of a sensitizer whose role is important to determine the type of mechanism. The use of a sensitizer such as a dye whose energy of excited triplet state can be transferred to the ground state oxygen produces singlet oxygen (Type II photooxygenation) [1]. This species adds to unsaturated substrates by [4+2] or [2+2] or ene-mode leading to endoperoxides or dioxetanes or allylic hydroperoxides, respectively (Scheme 30.1) [24].

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