54229-22-0Relevant articles and documents
DERIVATIVES OF NAPHTHALIC ACID. XIII. REACTION OF ANHYDRIDES AND IMIDES OF 4-SUBSTITUTED NAPHTHALIC ACID WITH 3-N-ALKYLAMINO- AND 3-N,N-DIALKYLAMINOPROPIONITRILES
Plakidin, V. L.,Vostrova, V. N.
, p. 2273 - 2281 (2007/10/02)
The anhydrides and imides of 4-(Br,Cl,NO2)-substituted naphthalic acid react with mono- and dialkylaminopropionitriles with substitution of the halogen atoms or nitro group by the alkylamino and dialkylamino groups and the formation of acrylonitrile.The eliminated halogen combines with the reagents in the form of a salt, which retards the formation of the main product.The rates of reaction of 4-bromonaphthalic anhydride with amines decreases with the amines in the order: (CH3)2NCH2CH2CN > (C2H5)2NCH2CH2CN > HN(C2H5)2 > N(C2H5)3.The nature of the substituted halogen (Br, Cl) and the substituent in the imide ring (H, CH3, C6H5) of the N-substituted 4-halogenonaphthalimides has little effect on the initial formation rate of the reaction product.The transition from o-xylene to isoamyl alcohol is accompanied by an increase of 2-3 orders of magnitude in the initial reaction rate.
