Catalyzed Rearrangements of Ten-Membered-Ring Allenes

Article abstract of DOI:10.1021/jo00160a016

Cyclodeca-1,2,5,8-tetraene (1) is shown to rearrange in the presence of various catalysts in acetic acid to cis,syn-tricyclo<4.4.0.0^2,4>deca-5,8-diene (5) which is accompanied in some cases by rearranged acetate products, principally cis,syn-bicyclo<4.4.0>deca-4,8-dien-2-yl acetate (3).Cyclodeca-1,2,5-triene (6) rearranges in a similar way, except that acetate product was only observed for Ag(I) catalysts.A related allene, bicyclo<7.1.0>deca-2,3-diene underwent normal oxymercuration without rearrangement.