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Issue 7, 2003
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1,3-Bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors

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Abstract

Cycloaddition and cyclodimerization reactions of 1,3-dibenzylidene- and 1,3-bis(p-methoxybenzylidene)-2-methylidenecyclohexanes, i.e., the diaryltrienes with fixed S-cis-configurations of exocyclic double bonds are studied. These compounds undergo in situ cyclodimerization of the [4+2]-type upon dehydration of the precursor tertiary alcohols and form endo-adducts in the Diels–Alder reaction with N-phenylmaleimide. In the presence of CF3COOH, acid-catalyzed cyclodimerization takes place leading to methylidene-substituted spirocyclodimers, which undergo intramolecular cyclization upon prolonged contact with CF3COOH to form a fused carbocyclic system containing a central, ‘three-petal’ fragment of six-membered rings.

Graphical abstract: 1,3-Bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors

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Supplementary files

Article information


Submitted
05 Nov 2002
Accepted
12 Feb 2003
First published
12 Mar 2003

Org. Biomol. Chem., 2003,1, 1210-1215
Article type
Paper

1,3-Bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors

E. I. Klimova, M. M. García, T. Klimova, S. H. Ortega and L. V. Bakinovsky, Org. Biomol. Chem., 2003, 1, 1210
DOI: 10.1039/B210890A

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