1057482-91-3Relevant articles and documents
Diels-alder approach to biaryls: Elucidation of competing tandem [2+2] cycloaddition/[1,3] sigmatropic shift pathway
Ashburn, Bradley O.,Carter, Rich G.,Zakharov, Lev N.
, p. 7305 - 7309 (2008)
(Chemical Equation Presented) Reaction of 2-halo-6-nitrophenylacetylene with an electron deficient diene gives rise to a [4+2] cycloaddition/ cycloreversion biaryl product and a bicyclo[4.2.0]octadiene resulting from a competing [2+2] cycloaddition pathway. The cyclobutene can be opened to give a mixture of cyclooctatriene and biaryl in varying amounts depending on heat and light exposure. The conversion of the cyclobutene into biaryl occurs through a [1,3] sigmatropic carbon shift followed by [4+2] cycloextrusion of ethylene gas.