Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 8, pp. 1424−1427.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
T.G. Kyazimova, E.G. Mamedbeili, A.V. Nagiev, Kh.I. Gasanov, G.G. Ivanova, 2009, published in Zhurnal Prikladnoi Khimii, 2009,
Vol. 82, No. 8, pp. 1324−1327.
AND INDUSTRIAL ORGANIC CHEMISTRY
T. G. Kyazimova, E. G. Mamedbeili, A. V. Nagiev, Kh. I. Gasanov, and G. G. Ivanova
Institute of Chemical Problems, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received November 11, 2008
Abstract—Hexachlorobicyclo[2.2.1]hepta-2,5-dienylmethyl haloacetates were prepared by [4+2]-cycloaddition
of hexachlorocyclopentadiene to the corresponding propargyl haloacetates.
Compounds of the bicyclo[2.2.1]heptene series exhibit
diverse useful properties. Rigid framework structures of
these compounds with ﬁ xed substituents are promising
models for studying structure–property relationships
Polyhalogenated bicyclic esters with other functional
groups are widely used for imparting ﬁ reproof properties
to polymeric materials, and also as modiﬁ ers, epoxy
resin hardeners, and biologically active substances [2, 3].
Halogen-containing functionally substituted norbornenes
are used as starting compounds for preparing important
commercial chemicals [4–7]. Studies of reactions
involving hexachlorocyclopentadiene (HCCPD) and
its derivatives, along with practical signiﬁ cance, are
of scientiﬁ c interest for elucidating the mechanism of
Diels–Alder reactions .
Proceeding with studies in the ﬁ eld of the synthesis of
polyhalogenated bicyclic esters [9–14], we prepared and
examined polyhalonorbornadienylmethyl haloacetates.
First, by the esteriﬁ cation procedure, we prepared propargyl
haloacetates IX–XV by the following scheme:
Table 1. The physicochemical properties of the esters prepared
R = CH
Cl (II, IX), CHCl
(III, X), CCl
Br (V, XII), CHBr
(VI, XIII), CBr