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The reaction of di-( o -acetylphenyl)acetylene ( 1 ) with excess dimethyl acetylenedicarboxylate (DMAD) produced bis-DMAD adducts  meso-3  and  rac-3 . This transformation is suggested to involve thermal rearrangement of  1  to the intermediate 3,3'-dimethyl-1,1'-biisobenzofuran ( A ), and subsequent Diels-Alder cycloadditions of two equivalents of DMAD to  A . The isolation of trapping products  meso-3  and  rac-3 , which contain complex polycyclic frameworks, provide strong evidence for the transient production of  A , the first biisobenzofuran. An X-ray crystal structure of  meso-3  was obtained.

Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran