AN APPROACH TO TRICYCLO4.7> TETRADECAHEPTA-1,3,5,7,9,11,13-ENE (BENZOCYCLOBUTA CYCLOOCTATETRAENE) UNUSUAL THERMAL REARRANGEMENTS IN THE C14H10 MANIFOLD

Article abstract of DOI:10.1016/0040-4020(82)85018-7

In an attempt to prepare the title compound 2 we have discovered that the isomeric 1,2-bis(but-1-en-3-ynyl)-benzenes and some of their silylated and deuterated derivatives 6a-d are converted to 2-(but-1-en-3-ynyl)naphthalenes 9a-d.Deuterium and silyl labeling experiments point to the operation of at least two mechanisms in these rearrangements.Heats of formation estimates make it feasible that 2 is an intermediate in one of them.