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Paper | Regular issue | Vol 38, No. 3, 1994, pp.629-640
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6619
Participation of Superjacent and Subjacent Orbitals for the Cycloaddition Reaction of 2H-4,9-Methanocycloundeca[b]furan-2-one with Electron-Deficient Dienophiles

Hiroki Tomioka and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


Cycloaddition reactions of 2H-4,9-methanocycloundeca[b]furan-2-one with dimethyl acetylenedicarboxylate (DMAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) were studied. The former reaction underwent a [12+2] cycloaddition, but the latter, only a [4+2] and a plausible [12+2] cycloadditions. The similar reaction of 2H-cyclohepta[b]furan-2-one with DMAD underwent a [4+2] and an [8+2] cycloaddition in a ratio of 8:1, while that with PTAD, only [4+2] cycloaddition. The periselectivity of the reactions was discussed on the basis of the MNDO calculations.