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Butadiyne-bridged [4 4 ]- and [4 8 ]metacyclophanes having exo-annular t-butyl groups were prepared by intermolecular Eglinton coupling of the dimeric unit or by intramolecular ring closure of the linear tetramer. Comparison of the 1 H and 13 C NMR spectra of [4 4 ]metacyclophane with those of [4 8 ]cyclophane and diphenylbutadiyne revealed its...
Dialkynylmethylenebicyclo[4.3.1]deca-1,3,5-triene derivatives were synthesized as precursors to generate dialkynylvinylidenes by extrusion of an aromatic fragment, indane. Photolysis of the trienes gave linear polyynes as the major products produced by rearrangement of the vinylidenes, together with the isomerization products having a methylenecycloheptatriene moiety.
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