Unusual hydroxyl effect on fulvene endoperoxide decompositions.

ABSTRACT: The thermal decomposition of fulvene endoperoxides ordinarily proceeds via an allene oxide intermediate affording oxepin-2(3H)-one derivatives. We have now uncovered new, unusual pathways in these decompositions where the presence of a hydroxyl group on the alkyl or aryl attached to the fulvene exocyclic double bond has a profound effect on the fate of the reactive intermediates derived from the unstable endoperoxides. Computational work supports the proposed mechanistic pathways.

SUBMITTER: Erden I 

PROVIDER: S-EPMC4860729 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature