
TY  - JOUR
A1  - Norris, RK 
A1  - Randles, D 
T1  - The Effect of Steric Hindrance on Radical and Ionic Substitution Reactions of Nucleophiles with Some &#945;-Alkyl-<I>p</I>-Nitrobenzyl Chlorides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 7
SP  - 1487
EP  - 1509
KW  - 
UR  - https://doi.org/10.1071/CH9791487 
N2  - The reactions of the &#945;-alkyl p-nitrobenzyl chlorides, p-NO2C6H4CH(CI)R(R = Me, Pr1, But), with nucleophiles, e.g, nitrite, nitroethanide, benzenethiolate and p-toluenesulfinate ions and the anion derived from diethyl 2-methylmalonate, in dimethyl sulfoxide have been studied. When R = But, SRNl reactions take place and give, in the reaction with p-toluenesulfinate and the anion from diethyl 2-methylmalonate, extremely sterically crowded molecules, which, as a result of bond formation between the more hindered atom in the ambident nucleophile and the benzylic carbon, display dynamic 1H N.M.R. effects. The derivatives where R = Me or Pri undergo radical and/or ionic processes depending on the nucleophile being used. Pathways accounting for some of the unusual compounds produced, e.g. 5-methyl-3,5-bis(p-nitropheny1)-2-isoxazoline N-oxide and (E)- and (Z)-p-nitroiso-butyrophenone O-(p-nitrobenzoyl) oximes from reaction of nitrite ion with the &#945;-methyl and &#945;- isopropyl compounds respectively, are proposed. 
ER  -

