Synthesis of α,ω-Bis(pyrazol-3-yl)alkanes: I. 1,4-Bis(1-methyl-and 1-benzyl-5-chloro-1H-pyrazol-3-yl)-butanes from 1,1,10,10-Tetrachlorodeca-1,9-diene-3,8-dione and 1,1-Dimethyl-or Benzylhydrazine Abstract-First representatives of bis-2-chloro-and 2,2-dichlorovinyl ketones, 1,10-dichlorodeca-1,9-diene-3,8-dione and 1,1,10,10-tetrachlorodeca-1,9-diene-3,8-dione, were synthesized by reaction of hexanedioyl dichloride with acetylene and 1,1-dichloroethene, respectively, in the presence of AlCl 3 . 1,1,10,10-Tetrachlorodeca-1,9-diene-3,8-dione reacted with benzylhydrazine and 1,1-dimethylhydrazine to give 1,4-bis(1-benzyl-5-chloro-1H-pyrazol-3-yl)butane and 1,4-bis(5-chloro-1-methyl-1H-pyrazol-3-yl)butane, respectively.Organic compounds containing two and more pyrazole fragments attract considerable interest from both theoretical and practical viewpoints primarily due to the possibility of using them as ligands for the preparation of polynuclear complexes and coordination polymers possessing valuable properties [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Multitopic pyrazole-containing ligands are also used as sorbents and intermediate products for the synthesis of compounds exhibiting biological and catalytic activity, and they can be involved in self-assembly of supramolecular ensembles, etc. On the other hand, organic polypyrazole ligands were studied insufficiently because of their low accessibility; therefore, search for new synthetic approaches to such compounds remains an important problem [1-17].The most widely known are ensembles in which pyrazole ring is linked through the pyrrole-type nitrogen atom [1][2][3][4][5][6][7][8][9][10][11][12]. 4,4′-Bis-pyrazole systems are fairly accessible; they are synthesized by reactions of polyelectrophiles with pyrazoles, aldehydes, and ketones [13][14][15]. A number of 3(5)-methyl(ethyl)-substituted bis-pyrazoles bridged at the 5,5′(3,3′)-positions by alkanediyl, 1,4-methylenephenyl, and 1,4′-diphenyleneoxy(disulfido) spacers were obtained by reaction of the corresponding bis-β-diketones with hydrazine hydrate [16,17]. Thus chemoselective synthesis of 3,3′-bridged bis-pyrazoles attracts strong interest.We develop a novel approach to linearly bridged α,ω-bis(pyrazol-3-yl)alkanes via heterocyclization of difunctional halovinyl ketones. In the present communication we report on the synthesis of first representatives of difunctional 2,2-dichloro-and 2-chlorovinyl ketones, 1,1,10,10-tetrachlorodeca-1,9-diene-3,8-dione (II) and 1,10-dichlorodeca-1,9-diene-3,8-dione (III) by reactions of adipoyl chloride with 1,1-dichloroethene and acetylene, respectively, in the presence of aluminum chloride according to the procedure described in [18] (Scheme 1). The reactions were carried out in methylene chloride at -5 to 20°C (reaction time 8 h. Unlike known procedures for the synthesis of alkyl 2,2-dichlorovinyl ketones [18], dehydrochlorination of 1,1,1,10,10,10-hexachlorodecane-3,8-dione (I) was effected by treatment with triethylamine. The yields (unoptimized) of ketone...