Rearrangements of the Allyl Group in the Thermolysis of 1,8-Bis(allylthio)- and 1,8-Bis(allylseleno)naphthalene Monooxides via Through-space Interaction between Two Sulfur and Selenium Atoms

Article abstract of DOI:10.1016/0040-4020(95)00791-6

1,8-Bis(allylthio)-and 1,8-bis(allylseleno)naphthalene monooxides underwent facile multiallylic rearrangements to give 2-allyl-substituted naphtho<1,8-cd>-1,2-dithioles and naphtho<1,8-cd>-1,2-diselenoles under mild conditions via the sulfur-sulfur and selenium-selenium through-space interaction.The mechanism for the reaction has been determined by D-tracer and cross-over experiments.