Verdazyl Radicals as Substrates for Organic Synthesis: The Synthesis and Characterization of [12]-, [13]-, and [21]-Paraheteraphanes

2012 
A tandem intermolecular–intramolecular 1,3-dipolar cycloaddition sequence with the bis-azomethine imine derived from a para-aryl-substituted bis-verdazyl radical has been used to form a series of [n]-paraheteraphanes, which form exclusively by a [1+1] double cycloaddition reaction, with no evidence for the formation of the [2+2] quadruple cycloadduct products. 1H NMR spectroscopic studies show that rotation of the phenyl ring of these compounds is affected by the size and structure of the [n]-paraheteraphane cavity.
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