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:


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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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