Oxa-Di-π-Methane Rearrangement of β,γ-Unsaturated Ketones

Authored by: V. Jayathirtha Rao , Kolupula Srinivas

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/b12252-23

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Abstract

Carbonyl compounds played an important role and became part of the leading research domain of organic photochemistry. Particularly, β,γ-unsaturated carbonyl compounds have attracted more attention. These β,γ-unsaturated carbonyls exhibit a variety of photochemical processes like (a) acyl migration, (b) oxa-di-π-methane (ODPM) rearrangement, (c) decarbonylation, (d) epimerization, (e) cycloaddition, (f) Norrish type I and type II processes, (g) cis–trans (E–Z) isomerization, and (h) reduction. Among the various photochemical processes of β,γ-unsaturated carbonyls, the ODPM rearrangement has attracted the attention of various researchers. This is because photochemical ODPM rearrangement provides high yields of products having synthetic exploitation, good photochemical quantum yields, making complex molecules in a very simple way, maintaining excellent selectivity, understanding the role of various excited states (involving multiplicity), and also understanding the role and link between carbonyl and olefin chromophores within the molecule to predict the reactivity.

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