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Communication | Special issue | Vol 49, No. 1, 1998, pp.79-83
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S36
Cycloaddition Reactions of Oxaquadricyclane, Oxanorbornadiene, and Related Compounds with Cyclooctyne

Kiyoshi Matsumoto,* Hiroyuki Taketsuna, Yukio Ikemi, Akikazu Kakehi, Takane Uchida, and Shinichi Otani

*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan

Abstract

Dimethyl oxaquadricyclane-2,3-dicarboxylate (1) with cyclooctyne (CO) gave, via carbonyl ylide (3a), a mixture of the exo and endo 1:1 adducts (2a,2b) along with the novel 1:2 adduct (2c), whereas the carbocyclic analogs underwent [σ2s+σ2s+π2s]cycloaddition. The first examples of inverse electron demand homo-Diels-Alder reactions of oxa-, aza- and carbo-norbornadienes with CO were also described.