With Hexachloro-1,3-butadiene

Reactions of tellurium with hexachloro-1,3-butadiene at 250° produced letrachlorotelluro-phene in low yield . This reaction has not yet been used for the preparation of other tellurophenes. 

Fringuelli, G. Marino, A. Taticchi, Gazz. Chim. Ital. 103, 1041 (1973). 

Fringuelli, S. Gronowitz, A.B. Hornfeldt, 1. Johnson, A. Taticchi, Acta Chem. Scand., Scr. B 30, 605 (1976). 

5-Tetrachlorotellurophene A mixture of 38.3 g (0.3 mol) of finely powdered tellurium and 156g (0.6 mol) of tctrachloro-1,3-butadiene is shaken at 250° for 40 h. The mixture is cooled to 20° and extracted with concentrated hydrochloric acid to remove tellurium tetrachloride. The product is separated by distillation under vacuum yield 13 g (14%) b.p. 31°/0.02 torr. 

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Baggett JM, Berndt WO. 1984. Renal and hepatic glutathione concentrations in rats after treatment with hexachloro-1,3-butadiene and citrinin. Arch Toxicol 56 46-49. 

Harleman JH, Seinen W. 1979. Short-term toxicity and reproduction studies in rats with hexachloro-(1,3)-butadiene. Toxicol AppI Pharmacol 47 1-14. 

The 1H NMR spectra of the polymers were obtained with a Varian HR-300 spectrometer, at 110-120° C, using 5-10% solutions of polymer in hexachloro-butadiene. The effect of temperature and solvent on the H NMR spectrum of a cationically prepared poly(4-methyl-l-pentene) was investigated. Figure 1-3 show the results obtained with carbon disulfide, carbon tetrachloride, o-dichloro-benzene, p-dichlorobenzene, and hexachlorobutadiene. 

As shown in Figure 1.17, there are three possible dichloroethylene compounds, all clear, colorless liquids. Vinylidene chloride forms a copolymer with vinyl chloride used in some kinds of coating materials. The geometrically isomeric 1,2-dichloroethylenes are used as organic synthesis intermediates and as solvents. Trichloroethylene is a clear, colorless, nonflammable, volatile liquid. It is an excellent degreasing and dry-cleaning solvent and has been used as a household solvent and for food extraction (for example, in decaffeination of coffee). Colorless, nonflammable liquid tetrachloroethylene has properties and uses similar to those of trichloroethylene. Hexachloro-butadiene, a colorless liquid with an odor somewhat like that of turpentine, is used as a solvent for higher hydrocarbons and elastomers, as a hydraulic fluid, in transformers, and for heat transfer. 

Diels-Alder reaction. An important organic reaction for the synthesis of 6-membered rings discovered in 1928. It involves the addition of an ethyl-enic double bond to a conjugated diene, i.e., a compound containing two double bonds separated by one single bond, as in 1,3-butadiene (CH2=CH-CH=CH2) or cyclopentadiene. The ease of addition of the ethy lenic compound is greatly enhanced by adjacent carbonyl groups hence maleic anhydride reacts quantitatively with hexachloro-cyclopentadiene to form chlorendic anhydride. 

The undesirable effects of chlorinated pesticides and PCB are closely associated with their tendency to accumulate in the fatty tissues of animals, where they are found at concentrations rising to hundred of parts per million. By contrast, the concentrations reported for the C1-C2 chlorocarbons are of the order of a few parts per billion which is three to five orders of magnitude lower [43]. The significant compounds (Table 7) are chloroform and carbon tetrachloride, trichloroethylene, perchloroethylene and methyl chloroform. Methyl chloride, methylene chloride and ethylene dichloride were not detected but the analytical method used did not resolve lower MW compounds while traces of hexachloro-butadiene were found in some marine organisms from an area known to receive industrial effluents. The compounds found in the animals were also found in a few samples of marine algae but at the time of sampling, the analytical method for methyl chloride was not adequate to show its presence. 

Hexafluoro-2,5-dihydrofuran [24849-02-3] is distilled into sulfur trioxide [7446-11-9] at 25°C. Addition of trimethyl borate [121-43-7] initiates a reaction which upon heating and distillation leads to a 53% yield of difluoromaleic anhydride. Dichloromaleic anhydride [1122-17-4] can be prepared with 92% selectivity by oxidation of hexachloro-1,3-butadiene with SO in the presence of iodine-containing molecules (65). Passing vaporized... 

Bosma TNP, FHM Cottaar, MS Posthumus, CJ Teunis, A van Veidhuizen, G Schraa, AJB Zehnder (1994) Comparison of reductive dechlorination of hexachloro-l,3-butadiene in Rhine sediments and model systems with hydroxocobalamin. Environ Sci Technol 28 1124-1128. 

Chromium compounds interact synergistically or antagonistically with many chemicals. For example, potassium dichromate administered by subcutaneous injection potentiated the effects of mercuric chloride, citrinin, and hexachloro-1,3-butadiene on rat kidneys (USPHS 1993). Chromium effects were lessened by ascorbic acid and Vitamin E, and N-acetyl cysteine was effective in increasing urinary excretion of chromium in rats (USPHS 1993)... 

When hexachloro-1,3-butadiene (81) is reacted with four equivalents of n-butyllithium in diethyl ether, a series of lithiation and elimination reactions gives l,4-dilithio-l,3-butadiyne (82) in good yields (Scheme 30). Ijadi-Maghsoodi and Barton verified this by derivatization with various chlorosilanes in yields up to 94%". ... 

Dekant W, Vamvakas S, Henschler D, et al. 1988b. Enzymatic conjugation of hexachloro-1,3-butadiene with gultathione. Formation of 1 -(Glutathion-S-yl)-l, 2,3,4,4-pentachlorobuta-1,3-diene and 1,4-... 

In 1978, Weiler and Brennan [63] reported the use of racemic 4-zso-thiazolin-3-one-l-oxide (54) as a dienophile, the structure of which could be considered to be a cyclic sulfinyl acrylamide. It undergoes facile cycloaddition (temperatures under 60 °C are required) with cyclop entadiene, 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene, to afford only one product in each case (Scheme 28). Reactions with anthracene and hexachloro cyclop entadiene required temperatures above 100°C, and were effectively catalyzed by A1C13. Although the stereochemistry of the obtained adducts was not ascertained, the authors suggest that the major one is the result of an endo-approach, which must be favored on the basis of mechanistic considerations. 

Jonker et al. (1996) administered female rats with a mixture of 4 nephrotoxicants tet-rachloroethylene, trichloroethylene, hexachloro-1,3-butadiene, and 1,1,2-trichloro-... 

Hexachloro-1,3-butadiene is another representative of emission of industrial origin (Fig. 6C). The concentrations determined range between 3 and 1900 ng/g with a maximum value at a depth of 94 cm. Below and above this layer, similar average values of 170 ng/g were detected. Furthermore, a second concentration maximum at a depth of 18 cm is followed by slowly decreasing values towards the top layer. 

One of the best studied examples of GST involvement in the biosynthesis of toxic conjugates is the metabolism of the potent nephrotoxin hexachloro-1,3-butadiene (HCBD). This compound has no adverse effects in the liver but its toxicity has been shown to arise following the initial hepatic GST-catalyzed direct conjugation of HCBD with GSH. The product of this reaction, pentachlorobuta-dienyl-glutathione, is subsequently metabolized by y-glutamyl transpeptidase and... 

Fig. 12. Toxication reactions catalyzed by GST. Examples of compounds that are not detoxified by conjugation with GSH include (a) ethylene dibromide, (b) trichloroethene, (c) hexachloro-1,3-butadiene, and (d) benzyl isothiocyanate.

HEXACHLOROBUTADIENE or HEXACHLORO-l,3-BUTADIENE (87-68-3) C4C1 CliC=CClCCl=CCIj Combustible liquid (flash point 195°F/90°C autoignition temp 1125°F/607°C Fire Rating 1). Unless inhibited, may form unstable peroxides in storage. Reacts strongly with oxidizers, aliuninum powder may cause fire and explosion. Mixtures with bromine perchlorate forms heat-, friction-, and shock-sensitive explosive compound. Attacks aluminum, and some plastics and coatings decomposes rubber. Thermal decomposition releases toxic and irritating chloride fumes. On small fires, use dry... 

Hexachloro-1,3-butadiene (perchlorobutadiene) [87-68-3] M 260.8, b 144.1"/100mm, 210-212"/760mm, d 4 1.683, n D 1.5556. Wash the diene with four or five 1/lOth volumes of MeOH (or until the yellow colour has been extracted), then stir it for 2 hours with H2SO4, wash it with distilled water until neutral and filter it through a column of P2O5. Distil it under reduced pressure through a packed column. [Rytner Bauer JHw Chem Soc 82 298 1960, Beilstein 1IV 998.]... 

It is of interest to show that the experimental data points of many organic compounds from other families (especially liquids) closely fit the correlation defined by Eq. (20). The log values of low molecular weight alcohols are about 0.2-0.4 unit higher than values calculated from their solubilities by Eq. (20). Hexachloro-1,3-butadiene with log = 4.90 and log S = -5.01 (20) and other alkylhalides (44) are well represented by the above correlation. Similarly, the measured log A ow values of pentane, cyclopentane, cyclohexane, and cyclohexene (66) are in close agreement with values estimated from their sol-ubiliti (44), Lindane, with a solubility of 7.8 ppm at 25T (108), = 386 K,... 

Figure 7.11 Expanded proton NMR spectra of the a-methy resonances of the alternating copolymer (a) in hexachloro-1,3-butadiene and (b) in CDCI3. Reprinted with permission from A.M. Aerdts, J.W. de Haan and A.L. German, Macromolecules, 1993, 26, 8, 1965. 1993, ACS [141])...

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