TANDEM ELECTROCYCLIZATION-CYCLOADDITIONS OF 6-METHYL-6-VINYLFULVENE
Gabriel Cabrera Dorantes, Ihsan Erden.
San Francisco State, San Francisco, CA.
The 6-Vinylfulvenes are versatile and reactive substrates, yet their chemistry has remained mostly unexplored due to the paucity of general and high-yielding methods for their syntheses. Recently, we developed a general synthesis of a large number of 6-vinylfulvenes and decided to systematically explore their chemistry. The first in this series was the oxidative transformations of 6-methyl-6-vinylfulvene. We now report on the cycloadditions of dihydropentalenes, derived from the thermal 8-electrocyclization of 6-methyl-6-vinylfulvene, with tropone and tetracyclone, respectively. Spectroscopic characterization of the cycloadducts, as well as frontier orbital considerations governing the observed periselectivities will be presented.