505030-69-3Relevant academic research and scientific papers
Palladium(0)-catalyzed allylation of 2,2′-dihydroxybiphenyl by 1-ethenylcyclopropyl sulfonates: Preparation of 2,2′-bis(cyclopropylideneethoxy) biphenyls
Delogu, Giovanna,Salauen, Jacques,De Candia, Cristina,Fabbri, Davide,Piras, Pier Paolo,Ollivier, Jean
, p. 2271 - 2279 (2002)
Dipotassium salts of 2,2′-dihydroxybiphenyl derivatives underwent palladium(0) catalyzed regioselective allylation by sulfonic esters (mesylates, tosylates) of 1-ethenylcyclopropanol to produce, in good yields, 2,2′-bis(cyclopropylideneethoxy)biphenyls, which are of biological interest. Whilst the tetrapotassium salt of 2,2′,6,6′-tetrahydroxybiphenyl, formed the triadduct 2,2′-tris(cyclopropylideneethoxy)hydroxybiphenyl as its main product. An unexpected palladium-induced rearrangement of the monoadducts 2-(2-cyclopropylideneethoxy)-2′-hydroxybiphenyl derivatives into the 2-[2-(1-ethenylcyclopropyloxy)]-2′-hydroxybiphenyl derivatives occurred; while the minor diastereomer of the monoadduct 2-[(2-cyclopropylidene-1-trimethylsilyl)ethoxy]-6,6-dimethoxy-2′- hydroxybiphenyl upon standing in CDCl3, underwent Claisen rearrangement into the 2,2′-dihydroxy-6,6′-dimethoxy-3-(2-trimethylsilylethenyl) cyclopropylbiphenyl.
