Sesquifulvalene Trapping as a [12+2] Adduct with Tetracyanoethylene

Abstract
Sesquifulvalene (1) is a substance of considerable theoretical interest1 which is expected to have a significant contribution to its structure from the dipolar resonance form 1b,2 and hence an exceptionally low bond order for the central double bond. Although a wide variety of annelated and otherwise substituted sesquifulvalenes have been prepared and characterized,3 the parent substance has proved remarkably elusive. Very recently, a preparation of 1 in crystalline form has been reported, based upon elimination of an acetoxy-11,12-dihydrosesquifulvalene derivative.4

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