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Photocycloaddition of quinones to olefins: Mechanism and applications

Photochemical reactions between benzoquinones and alkylidenecyclohexanes proceed regioselectively. Regioselectivity is determined by the conformational properties of the cyclic olefin. Photocycloadducts thus obtained may be used for the construction of important alkaloidal frameworks in synthetically useful yields. Oxetane formation is likely to occur through concerted collapse of an exciplex that possesses considerable charge transfer character.

Identiferoai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/13773
Date January 1993
CreatorsRivera Fortin, Maria Angelica
ContributorsCiufolini, Marco A.
Source SetsRice University
LanguageEnglish
Detected LanguageEnglish
TypeThesis, Text
Format209 p., application/pdf

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