1,3-Bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors
Klimova, Elena I.; García, Marcos Martínez; Klimova, Tatiana; Ortega, S. Hernandez; Bakinovsky, Leon V.; Klimova Elena I.; Universidad Nacional Autónoma de México, Facultad de QuÃmica, Cd. Universitaria, Coyoacán; GarcÃa Marcos MartÃnez; Universidad Nacional Autónoma de México, Instituto de QuÃmica, Cd. Universitaria, Coyoacán; Klimova Tatiana; Universidad Nacional Autónoma de México, Facultad de QuÃmica, Cd. Universitaria, Coyoacán; Ortega S. Hernandez; Universidad Nacional Autónoma de México, Instituto de QuÃmica, Cd. Universitaria, Coyoacán; Bakinovsky Leon V.; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Журнал:
Organic & Biomolecular Chemistry
Дата:
2003
Аннотация:
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 Dielsâ 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, â three-petalâ fragment of six-membered rings.
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