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 inOrganic letters Vol. 10; no. 22; pp. 5207 - 5210
Main Authors Andreu, Inmaculada, Delgado, Julio, Espinós, Amparo, Pérez-Ruiz, Raul, Jiménez, M. Consuelo, Miranda, Miguel A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2008
Amer Chemical Soc
Subjects
Azetidines - chemistry
Chemistry
Chemistry, Organic
Cyclization
Electron Transport
Organometallic Compounds - chemistry
Physical Sciences
Quaternary Ammonium Compounds - chemistry
Science & Technology
Spectrophotometry, Ultraviolet
Stereoisomerism
Time Factors
AMINO-ACID
REPAIR
ENZYME
DNA PHOTOLYASE
LIGHT
RADICAL CATIONS
OXETANE
6-4 PHOTOPRODUCTS
MODEL
SALTS
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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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol802181u