Cycloreversion of Azetidines via Oxidative Electron Transfer. Steady-State and Time-Resolved Studies
Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c- 2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5 •+). Stepwise C−N and C−C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as fin...
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Published in | Organic letters Vol. 10; no. 22; pp. 5207 - 5210 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
20.11.2008
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c- 2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5 •+). Stepwise C−N and C−C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as final products. Mechanistic evidence is provided by quenching studies, using laser flash photolysis to generate 5 •+ from its neutral precursor. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol802181u |