CHEMICAL-PROPERTIES OF THE FULVENE RADICAL CATION - A CYCLOADDITION WITH 1,3-BUTADIENE
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The chemical reactivity of the fulvene radical cation has been measured and compared with those of the benzene and various acyclic isomeric radical cations. This was accomplished by studying their reactivities in ion-molecule reactions observed using ion cyclotron resonance spectrometry (ICR). The fulvene radical cation exhibits considerably different properties from the other [C6H6]+ isomers, and this is interpreted in terms of a unique structure for ionized fulvene which is not subject to ring opening or isomerization to benzene. One of the reactions of the fulvene cation, that with 1,3-butadiene, was examined in detail using dueterium and C-13 labeling. The intermediate complex has been assigned as a cycloadduct formed by an ionic analogue of a [6 + 4] cycloaddition. 1980, American Chemical Society. All rights reserved.