en
Scientific article
Letter
English

Evidence for homoquadricyclene, a possible carbon ylide

Published inTetrahedron letters, vol. 24, no. 2, p. 181-184
Publication date1983
Abstract

The endo-epimer of the formal homo-1,4 adduct of monochlorocarbene and norborna-2,5-diene on treatment with lithium 2,2,6,6-tetramethylpiperidide in THF in the presence of diphenylisobenzofurane (DPIBF) gave a single Diels-Alder adduct. The same cyclo-adduct was obtained by subjecting the homo-1,4 adduct of dibromocarbene and norborna-2,5-diene to lithiummethyl in THF. By single crystal X-ray analysis the adduct is shown to be the result of the normal Diels-Alder cyclo-addition of DPIBF to the least hindered side of tetracyclo[3.2.1.0.2,70.4,6]oct-2-ene, a novel anti-Bredt olefine, best considered as a carbon ylide.

eng
Citation (ISO format)
JEFFORD, Charles et al. Evidence for homoquadricyclene, a possible carbon ylide. In: Tetrahedron letters, 1983, vol. 24, n° 2, p. 181–184. doi: 10.1016/S0040-4039(00)81360-X
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ISSN of the journal0040-4039
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