The orientation of electrophilic substitution of some 2,4- and 2,6-dihaloacetanilides has been examined by NMR methods. Mixed acid nitration of 2,6-dichloro and 2-chloro-6-methylacetanilides gave predominantly the 3-nitro derivatives.
for a review see WepsterB.M. in Progress in Stereochemistry ed. KlyneW., and de la MareP. B. D., Butterworths Scientific Publications, London, 1958, p. 99.
2.
DadswellH.E., and KennerJ., J. Chem. Soc., 1927, 1102.
3.
WepsterB.M., and VerkadeP. E., Rec. Trav. Chim. Pays Bas., 1950, 69, 1393.
4.
GodfreyK.E., and ThriftR. I., J. Chem. Soc.(C), 1967, 400.
5.
PewsR.G., HunterJ. E., and WehmeyerR. M., Tetrahedron, 1993, 49, 4809.
6.
OrtonK.J. P., and ReedW. W., J. Chem. Soc., 1907, 91, 1543.
7.
HodgsonH.H., and KershawA., J. Chem. Soc., 1929, 2917.
8.
EvansE.B., MabbottE. E., and TurnerE. E., J. Chem. Soc., 1927, 1159.
9.
SmithA.E., and OrtonK. J. P., J. Chem. Soc., 1908, 93, 1242.
