Cycloreversion of Azetidines via Oxidative Electron Transfer. Steady-State and Time-Resolved Studies

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• 作者：Inmaculada Andreu ; Julio Delgado ; Amparo Espinó ; s ; Raul Pé ; rez-Ruiz ; M. Consuelo Jimé ; nez ; Miguel A. Miranda
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：November 20, 2008
• 年：2008
• 卷：10
• 期：22
• 页码：5207-5210
• 全文大小：202K
• 年卷期：v.10,no.22(November 20, 2008)
• ISSN：1523-7052

文摘

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.