
TY  - JOUR
A1  - Newcombe, PJ 
A1  - Norris, RK 
T1  - Substitution Reactions of Nitrothiophens. II. The Anomalous Reaction of 4-Nitro-2-thenylidene Diacetate with the 2-Nitropropan-2-ide Ion
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 8
SP  - 1709
EP  - 1716
KW  - 
UR  - https://doi.org/10.1071/CH9791709 
N2  - The reaction of 4-nitro-2-thenylidene diacetate with 2-nitropropan-2-ide ion gives rise to 4-nitro-2-thenaldehyde (6), which is converted into its Meisenheimer adduct (13), together with small amounts of 2-(2'-methylprop-1'-enyl)-4-nitrothiophen (a), 5-(1'-methyl-1'-nitroethyl)-2-(2-methylprop-1''-enyl)-4-nitrothiophen (9) and 2-methyl-1-[5'-(1''-methyl-1''-nitroethyl)-4'-nitro-2'-thienyl]-2-nitro- propyl acetate (10). Mechanistic routes relating the adduct (13), whose 1H and 13C N.M.R. data are presented, and the two other proposed intermediates, 5-(1'-methyl-1'-nitroethyl)-4-nitro-2-thenalde- hyde (11) and 2-methyl-2-nitro-1-(4'-nitro-2'-thienyl)propyl acetate (12), are discussed. 
ER  -

