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Verdazyl Radicals as Substrates for Organic Synthesis: The Synthesis and Characterization of [12]‐, [13]‐, and [21]‐Paraheteraphanes
Author(s) -
Cumaraswamy Abbarna A.,
Hamer Gordon K.,
Georges Michael K.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101754
Subject(s) - chemistry , cycloaddition , intramolecular force , imine , radical , intermolecular force , tandem , 1,3 dipolar cycloaddition , ring (chemistry) , stereochemistry , aryl , molecule , organic chemistry , alkyl , materials science , composite material , catalysis
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. 1 H 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.