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Paper | Regular issue | Vol 48, No. 5, 1998, pp.905-918
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8099
Cycloadditions of Mesitonitrile Oxide with Hydroxy- and Methoxy-substituted Stilbenes. A Directing Hydrogen Bonding Model

Antonino Corsaro,* Giuseppe Buemi, Ugo Chiacchio, Venerando Pistarà, and Antonio Rescifina

*Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, I-95125 Catania, Italy


The regioselectivity of the reaction of mesitonitrile oxide with o-hydroxystilbene in favour of the 5-(2-hydroxyphenyl) isomer (regioisomeric ratio 5:1) is accounted by a directing hydrogen bonding model, while for reactions of the p-hydroxy- and p-methoxystilbene which show a 2:1 ratio between the 5- and 4-regioisomer, an electron-donor effect is invoked. These phenomena of regioselectivity are supported by semiempirical AM1 calculations.