On metal catalyzed reactions of homotropylium ions

✍ Scribed by Philip Warner

• Book ID: 104247469
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 114 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96541-4

✦ Synopsis

Our intereat in the structure and reactivity of monohomotropylium ion' and it6 metal complexes' prompts us to remark on some literature exampler which my have these as intermediates. The Ag catalyzed addition of benzyne to cyclooctatetraene (COT)3 16 particularly noteworthy. The major product, II, was postulated to arise from collap6e of the homotropylium ion intenaediate, I. Uowever, any mechanism mu6t explain why the sterically preferable benzobullvalene, III, is not formed (in contrast to the type of product found in the uncatalyzed COT dimari6ation4), and vhy the collapcle of I does not lead to the eight-membered ring product, VI, which would be expected to be the rejor product on the bee16 of the known quenching tendencies of homotropylium ione. 5

We feel that the o-bound Ag cannot account for the anoxmlou6 reaction path observed,