TY - JOUR
T1 - Organic reactions in melts and solids. Part VIII. Reactions of diacylanilines with monobasic and dibasic carboxylic acids
AU - Michman, M.
AU - Frenkel, M.
PY - 1971
Y1 - 1971
N2 - Transacylation reactions in molten mixtures of NN-diacetylaniline, NN-dibenzoylaniline, and N-acetyl-N-benzoylaniline with carboxylic acids RCO2H (R = Ph, p-MeO·C6H4, p-NO 2·C6H4, Me, Et, CH2Cl, or CHCl2) have been studied. Transacylation reactions with NN-diacylanilines proceeded more readily than with mono-N-acylanilines. In the reaction of N-acetyl-N-benzoylaniline with aromatic acids at 100°the benzoyl group was a better leaving group than acetyl. Reactions of NN-diacylanilines with phthalic acid gave low yields of N-phenylphthalimide at 170°, and none below 150°. Phthalic anhydride reacted with NN-diacylanilines only in the presence of aluminium chloride.
AB - Transacylation reactions in molten mixtures of NN-diacetylaniline, NN-dibenzoylaniline, and N-acetyl-N-benzoylaniline with carboxylic acids RCO2H (R = Ph, p-MeO·C6H4, p-NO 2·C6H4, Me, Et, CH2Cl, or CHCl2) have been studied. Transacylation reactions with NN-diacylanilines proceeded more readily than with mono-N-acylanilines. In the reaction of N-acetyl-N-benzoylaniline with aromatic acids at 100°the benzoyl group was a better leaving group than acetyl. Reactions of NN-diacylanilines with phthalic acid gave low yields of N-phenylphthalimide at 170°, and none below 150°. Phthalic anhydride reacted with NN-diacylanilines only in the presence of aluminium chloride.
UR - http://www.scopus.com/inward/record.url?scp=37049122356&partnerID=8YFLogxK
U2 - 10.1039/J39710003856
DO - 10.1039/J39710003856
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AN - SCOPUS:37049122356
SN - 0022-4952
SP - 3856
EP - 3859
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
ER -