
TY  - JOUR
A1  - Fischer, A 
A1  - Henderson, GN 
A1  - Thompson, RJ 
T1  - Ipso nitration. XIX. Formation of cyclohexadiene adducts from nitration of 4-ethyltoluene and 1,4-diethylbenzene in nitric acid and acetic anhydride
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 6
SP  - 1241
EP  - 1247
KW  - 
UR  - https://doi.org/10.1071/CH9781241 
N2  - Nitration of 4-ethyltoluene in acetic anhydride at -20&#176; gives the diastereoisomers of 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dienyl acetate and of 4-ethyl-1-methyl-4-nitrocyclohexa-2,5-dienyl acetate. Similar nitration of 1,4-diethylbenzene gives the diastereoisomers of 1,4-diethyl-4-nitro-cyclohexa-2,5-dienyl acetate. Rearomatization of the adducts of p-ethyltoluene in trifluoroacetic acid-trifluoroacetic anhydride gives 4-ethyl-2-nitrotoluene from the 1-ethyl-4-methyl-4- nitro isomers and 4-ethyl-3-nitrotoluene from the 4-ethyl-1-methyl-4-nitro isomers. In aqueous methanol 2-ethyl- 5-methylphenyl acetate is obtained from the 1-ethyl-4-methyl-4-nitro isomers and 5-ethyl-2- methyl-phenyl acetate from the 4-ethyl-1-methyl-4-nitro isomers. 
ER  -

