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Halogen – metal exchange of 3‐substituted 1,2‐dibromoarenes: the use of long‐range J CH coupling constants to determine regiochemistry
Author(s) -
DiMichele Lisa,
Menzel Karsten,
Mills Paul,
Frantz Doug,
Nelson Todd
Publication year - 2006
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1891
Subject(s) - chemistry , regioselectivity , halogen , coupling constant , benzoic acid , metal , computational chemistry , stereochemistry , organic chemistry , alkyl , physics , particle physics , catalysis
Regioselective halogen/metal exchange reactions were carried out on a series of 3‐substituted‐ 1,2‐dibromoarenes. Product mixtures were quenched with CO 2 to form the corresponding benzoic acid analogs to facilitate HPLC and NMR analysis. Substitution at the 3‐position could readily be assigned on the basis of 2D HMBC long‐range correlations, while assignment at the 2‐position was not as straightforward. The use of three‐bond J CH coupling constant measurements, extracted from 1‐D 1 H coupled 13 C experiments, were necessary to render unequivocal regio assignments. Copyright © 2006 John Wiley & Sons, Ltd.