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American Chemical Society, Organic Letters, 22(14), p. 5700-5703, 2012

DOI: 10.1021/ol302717s

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Oxetane ring enlargement through nucleophilic trapping of radical cations by acetonitrile

Journal article published in 2012 by Raul Pérez Ruiz, María Consuelo Jiménez Molero ORCID, Miguel Ángel Miranda Alonso, Luis R. Domingo, M. Consuelo Jiménez, Miguel A. Miranda, José Antonio Sáez Cases
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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). ; MICINN (Grants CTQ-2010-14882, CTQ-2009-13699 and JCI-2010- 06204) ; CSIC (JAEDOC 101-2011) ; Generalitat Valenciana (Grant No. GV/2012/041-20120205) ; Pérez Ruiz, R.; Jiménez Molero, MC.; Miranda Alonso, MÁ.; Domingo, LR. (2012). Oxetane ring enlargement through nucleophilic trapping of radical cations by acetonitrile. Organic letters. 14(22):5700-5703. doi:10.1021/ol302717s. ; Senia ; 5700 ; 5703 ; 14 ; 22