Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 7, pp. 1336−1338.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
I.M. Kulieva, M.K. Mamedov, A.G. Azizov, R.V. Alieva, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83, No. 7,
Synthesis of New Monomers, Cyanomethylnorbornyl Acrylates
I. M. Kulieva, M. K. Mamedov, A. G. Azizov, and R. V. Alieva
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received December 3, 2009
Abstract—The [4+2]-cycloaddition of cyclopentadiene to methacrylonitrile and addition of acrylic acids to the resulting
exo-2-cyano-endo-2-methylnorborn-5-ene were studied. The possibility was explored of synthesizing cyano-
containing bicyclic acrylates suitable as reactive monomers for preparation of polymeric products.
There exist procedures for preparation of cyclo-
hexyl acrylate , norbornyl acrylate , dihydro-
dicyclopentadienyl acrylate , and adamantyl acrylate
 suitable as reactive monomers for synthesizing
practically valuable polymer products. The molecules
of acrylates containing functional groups impart speciﬁ c
properties to the resulting polymers, which make them
suitable for diversiﬁ ed applications. These include
preparation of super glues, optical lenses, printing inks,
paint and varnish materials, and plasticizers [5–8].
Here, we synthesized new cyano-containing
monomers via [4+2]-cycloaddition of cyclopentadiene
(CPD) to methacrylonitrile (MAN), followed by adding
acrylic acids to the resulting exo-2-cyano-endo-2-
methylnorborn-5-ene (CMN) (see the scheme).
The known reaction of CMN synthesis employs,
however, CPD as the initial component  which
undergoes dimerization at room temperature to a stable
compound, dicyclopentadiene (DCPD) .
To simplify the procedure of [4+2]-cycloaddition
of CPD to MAN we used commercial DCPD as raw
material. The reaction was run above 160°С at which
temperature DCPD decomposes with elimination of CPD
which further reacts with MAN to form the target CMN.
R=H (V, VII) and CH