Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 2, pp. 243−247.
Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.F. Burdukovskii, D.M. Mognonov, V.G. Kotlyarov, 2011, published in Zhurnal Prikladnoi Khimii, 2011, Vol. 84, No. 2, pp. 247−251.
AND INDUSTRIAL ORGANIC CHEMISTRY
Polyheteroarenes Based on Aromatic Imidoyl Chlorides
V. F. Burdukovskii, D. M. Mognonov, and V. G. Kotlyarov
Baikal Institute of Nature Management, Siberian Branch, Russian Academy of Sciences,
Ulan-Ude, Buryatiya, Russia
Received January 27, 2010
Abstract—Interaction of imidoyl chlorides with various diamines, bisphenols, and dicarboxylic acids was studied.
Aromatic imidoyl chlorides (AICs) constitute an
exceedingly interesting and as yet not fully understood
class of organic compounds. Being derivatives of imide
acids whose synthesis is highly difﬁ cult, AICs behave
in reactions with nucleophilic reagents similarly to
carboxylic acid chloroanhydrides [1, 2]. In contrast to
reactions involving the latter, which, as a rule, yield direct-
substitution products, the ﬁ nal products of nucleophilic
reactions with AICs are more diverse. This is due to the
tendency of primarily formed derivatives containing
C=N groups toward rearrangements, cyclizations,
and other transformations [3, 4]. This circumstance
predetermines researchers’ interest in application of
AICs as monomers for synthesis of polymers and in
studies of their polymer-analogous transformations.
Moreover, there is only scarce published evidence about
use of AICs to obtain macromolecular compounds.
The goal of our study was to develop new methods for
synthesis of polyheteroarenes from AICs and examine
whether their further transformation is possible.
As nucleophilic substrates were chosen diamines,
bisphenol, and aromatic dicarboxylic acids. The
transformations were performed in accordance with the
A study of the interaction of 4,4'-diaminodiphenyloxide
with N,N '-diphenylimidoylisophthaloyl chloride (Ia)
(reaction 1) demonstrated that the highest molecular
mass polyamidines (PADs) (II) are formed at a strictly
equimolar ratio between the reactants, temperatures
of 110–130°C, and reaction duration of 5–7 h. It was
shown that the molecular mass (MM) rapidly increases
during the ﬁ rst 3–5 h of synthesis, then its rise somewhat