scholarly journals Environment-friendly organic synthesis. The photochemical approach

2000 ◽  
Vol 72 (7) ◽  
pp. 1321-1326 ◽  
Author(s):  
Angelo Albini ◽  
Maurizio Fagnoni ◽  
Mariella Mella

Photochemical reactions are expected to have an increasing role in organic synthesis with the drive towards environment-friendly reactions. Some examples illustrating the scope and versatility of radical alkylation of electrophilic alkenes via photoinduced electron transfer are presented. A few applications in special fields are mentioned.

ChemInform ◽  
2001 ◽  
Vol 32 (1) ◽  
pp. no-no
Author(s):  
Angelo Albini ◽  
Maurizio Fagnoni ◽  
Mariella Mella

1999 ◽  
Vol 77 (10) ◽  
pp. 1655-1670 ◽  
Author(s):  
Dino Mangion ◽  
Donald R Arnold

The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6pi-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.Key words: photochemistry, photoinduced electron transfer, bond homolysis, radical ions, radicals, exciplexes.


1998 ◽  
Vol 102 (38) ◽  
pp. 7447-7451 ◽  
Author(s):  
Maksudul M. Alam ◽  
Masahiro Sato ◽  
Akira Watanabe ◽  
Takeshi Akasaka ◽  
Osamu Ito

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