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Issue 4, 1981
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The thermal elimination of iodine from some substituted α-iodonaphthalenes: a structural study

Abstract

Brief heating of a number of methyl 8-iodo-5,7-dimethoxy-2-naphthoate derivatives with a variety of added hydroxy-, methoxy-, or acetoxy-substituents in the 4- and 6-positions has been found to result in facile elimination of iodine in certain compounds but not others; subsequent examination of other aspects of the chemistry of the system have suggested this to be a solid state effect. Single crystal X-ray structure determinations have been carried out on a representative selection of compounds, suggesting that in those examples where elimination has been found to occur, intimate charge-transfer interactions between the conjugated systems of adjacent molecules arising from the nature of the crystal packing are responsible; in those compounds which do not eliminate iodine, similar interactions may also be found but are associated with substituent out-of-plane steric interactions which hinder relative movement of the naphthalene moieties in the lattice.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1981, 610-627
Article type
Paper

The thermal elimination of iodine from some substituted α-iodonaphthalenes: a structural study

D. W. Cameron, G. I. Feutrill, L. J. H. Pannan, C. L. Raston, B. W. Skelton and A. H. White, J. Chem. Soc., Perkin Trans. 2, 1981, 610
DOI: 10.1039/P29810000610

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