CYCLOADDITION BETWEEN 2,3,DIBROMO-5,6-TRINORBORNENOBENZOQUINONE AND 1,2-BIS(METHOXYCARBONYL)CYCLOBUTADIENE - INTERVENTION OF A FRAGMENTATION REACTION DURING GUEST FOR ANNULATED, FUNCTIONALIZED CUBANES
G. Mehta et Shk. Reddy, CYCLOADDITION BETWEEN 2,3,DIBROMO-5,6-TRINORBORNENOBENZOQUINONE AND 1,2-BIS(METHOXYCARBONYL)CYCLOBUTADIENE - INTERVENTION OF A FRAGMENTATION REACTION DURING GUEST FOR ANNULATED, FUNCTIONALIZED CUBANES, Journal of the Chemical Society. Perkin transactions. I, (20), 1994, pp. 2949-2951
Diels-Alder reaction between 1,2-bis (methoxycarbonyl) cyclobutadiene
2 and quinone 1 predominantly furnished adduct 5, which on photolysis
gave the annulated secopentaprismane dione 3. Attempted double-ring-co
ntraction on compound 3 took a devious course to furnish a fragmentati
on product 11 via tandem Haller-Bauer cleavage and fragmentation.