Oxetane Ring Enlargement through Nucleophilic Trapping of Radical Cations by Acetonitrile

Oxidative electron transfer cycloreversion of trans,trans-2-cyclopropyl-4-methyl-3-phenyloxetane, using triphenylthiapyrylium perchlorate as a photosensitizer, leads to distonic 1,4-radical cations; subsequent cleavage gives rise to fragmentation products (pathway a), whereas nucleophilic trapping b...

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Bibliographic Details
Published in:Organic letters 2012-11, Vol.14 (22), p.5700-5703
Main Authors: Pérez-Ruiz, Raúl, Sáez, Jose A, Domingo, Luis R, Jiménez, M. Consuelo, Miranda, Miguel A
Format: Article
Language:English
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Summary:Oxidative electron transfer cycloreversion of trans,trans-2-cyclopropyl-4-methyl-3-phenyloxetane, using triphenylthiapyrylium perchlorate as a photosensitizer, leads to distonic 1,4-radical cations; subsequent cleavage gives rise to fragmentation products (pathway a), whereas nucleophilic trapping by acetonitrile affords a ring expanded oxazine (pathway b).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302717s