Issue 2, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Diels–Alder cycloadditions of the N-vinylcarbazole radical cation

Nathan L. Bauld,a   Jingkui Yanga  and  Daxin Gaoa  

a Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas, USA

Abstract

The first radical cation Diels–Alder reactions of N-vinylcarbazole, the substrate for which radical cation cycloaddition (cyclodimerization) was first observed more than 30 years ago, have now been observed. The additions of N-vinylcarbazole to both cyclopenta-1,3-diene and cyclohexa-1,3-diene, catalyzed by tris(4-bromophenyl)aminium hexachloroantimonate, have been observed. Further, a two step mechanism for these cycloadditions has been established through the use of stereospecifically labelled substrate ((Z)-N-(2-deuteriovinyl)carbazole).

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Article information

DOI
https://doi.org/10.1039/A908659E
Article type
Paper
Submitted
01 Nov 1999
Accepted
18 Nov 1999
First published
25 Jan 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 207-210

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Diels–Alder cycloadditions of the N-vinylcarbazole radical cation

N. L. Bauld, J. Yang and D. Gao, J. Chem. Soc., Perkin Trans. 2, 2000, 207 DOI: 10.1039/A908659E

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