Rearrangement of a 2-Methylenecyclobutanone Derivative Triggered by Photoinduced Electron Transfer:  An Unprecedented Oxa Analogue of the Tetramethyleneethane Radical Cation

2004 ◽  
Vol 126 (2) ◽  
pp. 414-415 ◽  
Author(s):  
Hiroshi Ikeda ◽  
Futoshi Tanaka ◽  
Kimio Akiyama ◽  
Shozo Tero-Kubota ◽  
Tsutomu Miyashi
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer

Photoinduced electron-transfer reactions: rearrangement of a bicyclopropenyl radical cation

1985 ◽  
Vol 107 (13) ◽  
pp. 3840-3843 ◽  
Author(s):  
Christopher J. Abelt ◽  
Heinz D. Roth
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer ◽  
Transfer Reactions ◽  
Electron Transfer Reactions

Photochemical Doping of TCNQ by Photoinduced Electron Transfer and C-C Cleavage of Radical Cation

1999 ◽  
Vol 28 (3) ◽  
pp. 241-242 ◽  
Author(s):  
Hajime Yokoi ◽  
Katsuya Ishiguro ◽  
Yasuhiko Sawaki
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer

ChemInform Abstract: Radical Cation Cycloaddition Reactions of 2-Vinylbenzofurans and 2-Vinylfurans by Photoinduced Electron Transfer.

ChemInform ◽  
2010 ◽  
Vol 29 (23) ◽  
pp. no-no
Author(s):  
J. BOTZEM ◽  
U. HABERL ◽  
E. STECKHAN ◽  
S. BLECHERT
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer ◽  
Cycloaddition Reactions

Products from photochemical reactions and electrochemical oxidation of methylenecyclopropane

1997 ◽  
Vol 75 (12) ◽  
pp. 1795-1809 ◽  
Author(s):  
H.J.P. de Lijser ◽  
T. Stanley Cameron ◽  
Donald R. Arnold
Keyword(s):  
Electron Transfer ◽  
Ionization Potential ◽  
Radical Cation ◽  
Photoinduced Electron Transfer ◽  
Nucleophilic Addition ◽  
Major Product ◽  
Oxidation Potential ◽  
Photochemical Reactions ◽  
Tert Butyl ◽  
Adiabatic Ionization Potential

The reactivity of methylenecyclopropane (MCP, 1) and its radical cation (1+•) have been studied in the presence and absence of a nucleophile (methanol). Photochemical reactions of 1 in the presence of an electron-acceptor (1,4-dicyanobenzene, 6) and a codonor (biphenyl, 7) in acetonitrile (with and without methanol present) or chloroform lead to cycloadditions (ortho, meta, and para; products 12–17) rather than products from photoinduced electron transfer (PET). Based on the measured (cyclic voltammetry, CV) oxidation potential, using the Weller equation, electron transfer (ET) was predicted to occur. It was shown that the measured oxidation potential of 1 represents the adiabatic ionization potential. For PET processes the value for the vertical ionization potential must be used. Electrochemical (EC) generation of 1+• without a nucleophile present results in the formation of one major product: tert-butyl acetamide (25). A series of rearrangements leading to the tert-butyl cation is proposed. Addition of a nucleophile (methanol) to the mixture leads to the formation of 3-methoxy-2-(methoxymethyl)-1-propene (26). This product may arise from trapping of the initially formed ring-opened (trimethylenemethane) radical cation (1a+•), which undergoes a second oxidation and nucleophilic addition (ECE). Keywords: methylenecyclopropane, radical cation, photochemistry, electrochemistry, photocycloaddition.

scholarly journals Radical Cation Cycloaddition Reactions of 2-Vinylbenzofurans and 2-Vinylfurans by Photoinduced Electron Transfer.

1998 ◽  
Vol 52 ◽  
pp. 175-193 ◽  
Author(s):  
Jörg Botzem ◽  
Udo Haberl ◽  
Eberhard Steckhan ◽  
Siegfried Blechert ◽  
Inger Søtofte ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer ◽  
Cycloaddition Reactions

Photoinduced electron transfer reactions of chloranil with small-ring hydrocarbons. Contrasting reactivities of radical cation intermediates

1997 ◽  
Vol 109 (2) ◽  
pp. 119-124 ◽  
Author(s):  
William Bergmark ◽  
Suzanne Hector ◽  
Guilford Jones ◽  
Churl Oh ◽  
Tsutomu Kumagai ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Radical Cation ◽  
Photoinduced Electron Transfer ◽  
Transfer Reactions ◽  
Small Ring ◽  
Electron Transfer Reactions
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