Photochemical Formation of Novel Pyrrolo[3,2-b]-6,7-benzobicyclo[3.2.1]octa- 2,6-diene

The first synthesis of 1,4,9,10-tetrahydro-4,9-methanobenzo[4,5]cyclohepta[1,2-b]pyrrole (11) was achieved by the photochemical intramolecular [2 + 2] cycloaddition of N-phenoxycarbonyl- (5a) and N-ethoxycarbonyl-2-[2-(2-vinylphenyl)]pyrrole (6a), respectively, followed by basic hydrolysis of the is...

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Veröffentlicht in:Journal of organic chemistry 2003-09, Vol.68 (19), p.7524-7527
Hauptverfasser: BASARIC, Nikola, MARINIC, Zeljko, SINDLER-KULYK, Marija
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Sprache:eng
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Zusammenfassung:The first synthesis of 1,4,9,10-tetrahydro-4,9-methanobenzo[4,5]cyclohepta[1,2-b]pyrrole (11) was achieved by the photochemical intramolecular [2 + 2] cycloaddition of N-phenoxycarbonyl- (5a) and N-ethoxycarbonyl-2-[2-(2-vinylphenyl)]pyrrole (6a), respectively, followed by basic hydrolysis of the isolated N-substituted 1,4,9,10-tetrahydro-4,9-methanobenzo[4,5]cyclohepta[1,2-b]pyrroles (10a, 10b). Some competitively formed products were also isolated.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0346454