Reaction Control in Synthetic Organic Photochemistry: Switching between [5+2] and [2+2] Modes of Cycloaddition

Split personality: Reaction conditions that enable powerful control over the mode of photocycloaddition in maleimides have been developed. Direct irradiation favors the [5+2] mode whereas sensitized irradiation allows a complete switch to the [2+2] mode (see scheme; TBS=tert‐butyldimethylsilyl).

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-11, Vol.48 (46), p.8716-8720
Main Authors: Roscini, Claudio, Cubbage, Kara L, Berry, Malcolm, Orr-Ewing, Andrew J, Booker-Milburn, Kevin I
Format: Article
Language:English
Subjects:
alkenes
Alkenes - chemistry
Azepines - chemical synthesis
Azepines - chemistry
Cyclization
cycloaddition
Cyclobutanes - chemical synthesis
Cyclobutanes - chemistry
maleimides
Maleimides - chemistry
Molecular Structure
Photochemistry
sensitizers
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Summary:Split personality: Reaction conditions that enable powerful control over the mode of photocycloaddition in maleimides have been developed. Direct irradiation favors the [5+2] mode whereas sensitized irradiation allows a complete switch to the [2+2] mode (see scheme; TBS=tert‐butyldimethylsilyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904059