Molecular orbital calculations and carbon-13 NMR studies to explain a regiospecific demethylation of 3-alkyl-1, 2-dimethoxybenzenes

…, N Pourahmady, GJ Mains, EJ Eisenbraun

Index: Jardon, Phillip W.; Vickery, Euin H.; Pahler, Leon F.; Pourahmady, Naser; Mains, Gilbert J.; Eisenbraun, Edmund J. Journal of Organic Chemistry, 1984 , vol. 49, # 12 p. 2130 - 2135

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Citation Number: 27

Abstract

This study was performed to explain a regiospecific demethylation of 3-alkyl-1, 2- dimethoxybenzenes. PRDDO-MO calculations show that the low-energy conformation of the carbon of a methoxy group having two ortho neighbors on a benzene ring is located out of the plane of the aromatic ring, whereas a methoxy group with only one ortho neighbor executes restricted rotation in the plane of the ring. The carbon portion of the methoxy ...