Issue 5, 2002

Stereochemical and electronic features of the [3 + 2] cycloaddition of pentafulvenes with acylnitrones

Abstract

A series of mono- and di-substituted pentafulvenes 1–3 was reacted with aroylnitrones 4 to afford the corresponding fused bicyclic monoadducts 5–9, generally as a mixture of isomers. The stereochemistry of the addition reaction was established by 1D and 2D NMR spectroscopies or X-ray crystallography. Performance of theoretical calculations has been undertaken in order to rationalize the important differences in regioselectivity displayed by the reaction.

Graphical abstract: Stereochemical and electronic features of the [3 + 2] cycloaddition of pentafulvenes with acylnitrones

Article information

Article type
Paper
Submitted
30 Jul 2001
Accepted
07 Jan 2002
First published
31 Jan 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 687-695

Stereochemical and electronic features of the [3 + 2] cycloaddition of pentafulvenes with acylnitrones

F. Djapa, K. Ciamala, J. Melot, J. Vebrel and G. Herlem, J. Chem. Soc., Perkin Trans. 1, 2002, 687 DOI: 10.1039/B106892J

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