Butterflyene: an entry into an aesthetically pleasing carbocycle via a Diels-Alder reaction on a tetrasubstituted olefin.

ABSTRACT

An interesting molecular architecture, butterflyene, resembling the shape of a butterfly has been synthesized via a sequence of cyclocondensation, benzylic oxidation, McMurry coupling and Diels-Alder reaction (DAR), successively. The DAR of the tetrasubstituted double bond of a bicyclopentylidene moiety with various dienes has been performed to prepare the analogues of butterflyene. DFT calculations have also been used to analyze the structural optimization and reaction energies.