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- Title
Regioselective palladium-catalyzed ring-opening reactions of C<sub>1</sub>-substituted oxabenzonorbornadienes.
- Authors
Raheem, Mohammed Abdul; Edmunds, Michael; Tam, William
- Abstract
The effect of ethyl and methoxycarbonyl substitution on the C1 position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl iodide nucleophiles. Electron-withdrawing groups in the C1 position or on the aryl iodide afforded lower yields and led to aromatization of products. The presence of an electron-donating group in either position provided high yields in all cases. Despite variances in electronic nature, all trials produced a single regioisomeric product resulting from addition of the aryl group to the olefin carbon farthest from the C1 substituent. Based on these findings, a mechanism has also been proposed.
- Subjects
METHOXYCARBONYL group; NUCLEOPHILIC reactions; AROMATIZATION catalysts; ARYL iodides; OLEFINATION reactions; SUBSTITUTION reactions
- Publication
Canadian Journal of Chemistry, 2014, Vol 92, Issue 9, p888
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2014-0217