Add time:07/29/2019         Source:sciencedirect.com

The lithiation of 4,4′-dibromooctafluorobiphenyl with n-butyllithium to yield 4,4′-dilithiooctafluorobiphenyl and 4-lithio-4′-bromooctafluorobiphenyl as a by-product under various conditions is described. It is proposed that thermal decomposition of the lithiated products formed at low temperatures (−80° to −90°) leads to products originating principally by nucleophilic displacement reactions, while rapid thermal decomposition, after metal-halogen interconversion at temperatures of 0°, leads principally to products originating by elimination reactions. The intermediacy of benzyne species is proposed on the basis of observed addition reactions with furan to give the adduct 1,1′,3,3′,4,4′-hexafluoro-5,8,5′,8′-tetrahydro-2,2′-binaphthyl 5,8,5′,8′-diepoxide.

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