Borane-induced ring closure reaction of oligomethylene-linked bis-allenes.

ABSTRACT: The trimethylene-linked bis-allene 3a reacts with Piers' borane [HB(C₆F₅)₂] by a hydroboration/allylboration sequence to generate the cyclization product 5a. Its pyridine adduct was isolated and characterized by X-ray diffraction. Compound 5a undergoes a typical frustrated Lewis pair 1,2-P/B alkene addition reaction with PPh₃ to give the heterobicyclic bridged olefinic zwitterionic product 9a. The tetramethylene-linked bis-allene 3b and its phenylene annulated analogue 3c react with HB(C₆F₅)₂ to give the analogous seven-membered ring products 5b,c under mild conditions. The cyclization product 5a undergoes a series of sequential allylboration reactions with t

SUBMITTER: Tao X 

PROVIDER: S-EPMC8148058 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature