Ariffin, Azhar and Hadi, A.H.A. and Thomas, N.F. and Kee, C.H. and Awang, Khalijah and Weber, J.F.F. and Lim, C.G. and Mukhtar, M.R. (2008) The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline. Heterocycles, 75 (5). pp. 1097-1108. ISSN 0385-5414,
Full text not available from this repository.Abstract
The addition of benzophenone to a FeCl(3)/CH(2)Cl(2) mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction conditions. A catalytic cycle has been proposed that involves not only stilbene radical cations but also Fe(2+) promoted benzophenone ketyl radical formation which enhances cyclisation, suppresses dimerization and accounts for the virtually quantitative recovery of the benzophenone.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Additional Information: | Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA |
| Uncontrolled Keywords: | radical cation, benzophenone, ketyl radical, maleic anhydride, oxidative cyclization, fecl3-promoted synthesis, alkaloids, derivatives, construction, dimerization, duocarmycins, cc-1065 |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Miss Malisa Diana |
| Date Deposited: | 03 Jul 2013 02:32 |
| Last Modified: | 01 Mar 2019 09:05 |
| URI: | http://eprints.um.edu.my/id/eprint/8070 |
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