
TY  - JOUR
A1  - McLure, FI 
A1  - Norris, RK 
T1  - The Stereochemistry of S<sub>RN</sub>1 Reactions in Nitroacenaphthenes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1987
VL  - 40
IS  - 3
SP  - 523
EP  - 537
KW  - 
UR  - https://doi.org/10.1071/CH9870523 
N2  - The reaction of the 2-chloro-1,l-dialkyl-6-nitroacenaphthenes (1)-(3) with azide and p- toluenethiolate ions takes place by the SRN1 mechanism, to give the substitution products (27)-(32), despite the fact that the nitro group and the chlorine-bearing benzylic carbon are attached to different aromatic rings. The reaction of the stereoisomers (2) and (3) of 2-chloro-1-ethyl-1-methyl-6-nitroacenaphthene takes place through an effectively planar benzylic radical (35), which is preferentially attacked from the face remote from the a-ethyl group. The presence of geminal alkyl groups &#945; to the reaction site in the rigid acenaphthene system restricts the scope of the substitution processes to sterically unhindered nucleophiles, and the reaction fails with reagents such as sodium p- toluenesulfinate (23) and the salts, (24) and (25), derived from 2-ethylmalononitrile and 2-nitropropane. 
ER  -

