Cycloaddition between 2,3-dibromo-5,6-trinorbornenobenzoquinone and 1,2-bis(methoxycarbonyl)cyclobutadiene: intervention of a fragmentation reaction during quest for annulated, functionalized cubanes

Mehta, Goverdhan ; Reddy, S. Hari Krishna (1994) Cycloaddition between 2,3-dibromo-5,6-trinorbornenobenzoquinone and 1,2-bis(methoxycarbonyl)cyclobutadiene: intervention of a fragmentation reaction during quest for annulated, functionalized cubanes Journal of the Chemical Society, Perkin Transactions 1 (20). pp. 2949-2951. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1994...

Related URL: http://dx.doi.org/10.1039/P19940002949

Abstract

Diets-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-contraction on compound 3 took a devious course to furnish a fragmentation product 11via tandem Haller-Bauer cleavage and fragmentation.

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