Hexachloro-1,3-cyclopentadiene

Hexachloro-1,3-cyclopentadiene dimerb dodecachlorooctahydro-1,3,4-metheno-1 H-cyclobuta[cd] pentaleneb... 

Hydrazine hydrate (29.4 mL, 30.32 g, 0.61 mole) is added dropwise from a pressure-equalizing addition funnel to a cooled (0°) solution of hexachloro-1,3-cyclopentadiene (16 mL, 27.3 g, 0.10 mole) in 200 mL of methanol in a 500-mL Erlenmeyer flask. The solution turns dark red immediately. After the addition, the flask is securely stoppered (with a glass stopper) and the solution is stirred in the dark for 5 days at 5°, during which time a red solid collects on the walls of the flask. The mixture is poured into 5 L of water and filtered. The solid is air dried, dissolved in diethyl ether, and filtered. The filtrate is evaporated to dryness and the residue is extracted with cyclohexane in a Soxhlet extractor. The solution is concentrated and cooled and the red-brown crystals are filtered off. Additional product can be obtained by washing the material remaining in the thimble with water and extracting again with cyclohexane. Total yield 15 g (65%). 

Synonyms/Trade Names HCCPD Hexachloro-1,3-cyclopentadiene 1,2,3,4,5,5-Hexachloro-1,3-cyclopentadiene Perchlorocyclopentadiene... 

Hexachlorocyclopentadiene-cyclooctadiene adduct. See Dodecachloro dodecahydro dimethanodibenzo cyclooctene Hexachlorocyclopentadiene dimer 1,2,3,4,5,5-Hexachloro-1,3-cyclopentadiene dimer. See Perchloropentacyclodecane 2,2, 3,3, 5,5 -Hexachloro-6,6 -dihydroxydiphenylmethane. See Hexachlorophene... 

Steric effects play a dominant role with more highly substituted dienes. Hexachloro-cyclopentadiene, for example, shows a higher endo preference than cyclopentadiene because the 5-chlorine causes steric interference with exo substituents.13... 

Endrin is a stereoisomer of dieldrin produced by the reaction of vinyl chloride and hexachloro-cyclopentadiene to yield a product which is then dehydrochlorinated and condensed with cyclopentadiene to produce isodrin. This intermediate is then epoxidized with peracetic or perbenzoic acid to yield endrin. An alternative production method involves condensation of hexachlorocyclopentadiene with acetylene to yield the intermediate for condensation with cyclopentadiene (EPA 1985e IARC 1974). 

Rats given 6 mg kg hexachlorocyclopentadiene orally excreted 33% in urine and 10% in feces in 7 days. Most excretion occurred during the first 24 h after dosing. The kidney retained 0.5% and the liver >0.5%. Biliary excretion of only 16% with 66% still voided in the feces of bile duct cannulated rats suggested that the majority of orally consumed was not absorbed. Degradation apparently occurred in the gut since little of the fecal material was of an apolar nature. The kidney, liver, ovaries, and fat were the major sites of deposition of C-hexachloro-cyclopentadiene equivalents. In rats, the kidney contained the highest levels of residues, whereas in mice the residues in the liver exceeded those in the kidney. Other than this difference, the fate of hexachlorocyclopentadiene in rats and mice, both male and female, was quite similar and in each case the tissue residues reached a plateau after about 2 weeks on the hexachlorocyclopentadiene-containing diets. 

In another study, rats were either exposed to hexachlorocyclopentadiene vapors for 1 h, or were dosed orally with " C-hexachlorocyclopentadiene in corn oil. Tissue, urine, and feces samples were analyzed, as well as expired air, to assess the fate and retention time. Approximately 84% of the inhaled compound is retained. Inhaled " C-hexachloro-cyclopentadiene was excreted in the urine orally administered " C-hexachlorocyclopentadiene was eliminated in the feces. In rats exposed by inhalation, the trachea and lung had the highest residue accumulation. In animals receiving oral doses kidneys and liver were major sites of accumulation. These studies indicate that the route of exposure is critical to the pattern of retention and elimination. 

Tetrachlorocyclopentadienone (3). This reactive Diels-Alder diene is unknown as the monomer but can be generated starting with the readily available hexachloro-cyclopentadiene (1, Hooker Chem. Corp., Aldrich). Newcomer and McBee found... 

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. 

Preparation. The reagent is prepared in good yield by reaction of hexachloro-cyclopentadiene with ethylene glycol and potassium hydroxide.1,2... 

Irradiation into this transition causes the almost quantitative formation of ferricenium tetrachloroferrate [ (C 5H 5) 2Fe] [FeCl 4] 296,301) This product can also be obtained radiation-chemically from Fn and CCI4 294,299,300.301) [see section L2], by reacting Cl2 with excess Fn 301> 54°), by treating Fn with FeCl3 541>, by heating Fn with hexachloro-cyclopentadiene to 90—120 °C 542> or by illuminating this mixture 430>. 

Diels-Alder adduct of cyclopentadiene and penta-chlorocyclopentadiene, 1% hexachloro-cyclopentadiene, 1% octachlorocyclopentene, and 15.5% miscellaneous constituents. Oxy-chlordane and heptachlor epoxide are toxi-cologically significant degradation products (Figure 7.1). 

The thermal behavior of A and B above 150°C has been studied. Both in the gas phase and in solution, each compound yields a 3 5 mixture of trans,cis-1,5-cyclooctadiene (C) and cw-cis-l,5-cyclooctadiene (D). When hexachloro-cyclopentadiene is present, compound E is found in place of C, but the amount of D formed is about the same as in its absence. Formulate a description of the thermolysis mechanism that is consistent with these facts and the general theory of thermal electrolytic reactions. 

Its in situ formation in the presence of water, methanol, or dimethylamine provides the corresponding add, ester, or amide. Allyl 2>chlorotexafluoro> cyclopentenyl ether, prepared by the reaction of allyl alcohol with 1,2 dichlorohexafluorocyclopentene and sodium hydroxide, rearranges at 95 °C (Scheme 17). The Diels-Alder adduct of the product with hexachloro-cyclopentadiene is said to possess pestiddal activity. The adduct of allyl... 

The following sections concern the use of a chlorinated flame retardant (CFR) in plastics. CFR consists of the Diels-Alder adduct of hexachloro-cyclopentadiene and 1,5-cyclo-octadiene. Some experimental results are given, without the proposal of any mecharusms, which exemplify the flame retardancy improvements obtainable by various synergistic combinations. 

The following cycloaliphatic compounds are suitable as flame retardants in polyolefins hexabromo-cyclododecane and bromine-containing Diels-Alder reaction products based on hexachloro-cyclopentadiene. 

Semi- or non-volatile chlorinated organic Compounds, hexachloro-butadiene, hexachloro-cyclopentadiene, octa. chlorocyclopentadiene, hexachlorobenzene Extractions performed on homogeniser using hexane, hexane -benzene or hexane -toluene Purge and trap method, recoveries 88-125% 0.1 ppb [189]... 

Endrin [72-20-8] is l,2,3,4,10,10-hexachloro-l,4,4t ,5,8,8t -hexahydro-6,7-epoxy-l,4- <7o, <7o-5,8-dimethanonaphthalene (35) (mp 245 dec, vp 0.022 mPa at 25°C) and is soluble in water to 23 / g/L. It is produced by a Diels-Alder reaction of hexachloronorbomadiene with cyclopentadiene, followed by epoxidation. This reaction produces the endo,endo isomer of dieldrin, which is less stable and more toxic with rat LD q values of 17.8 and 7.5 (oral) and 15 (dermal) mg/kg. It is used as a cotton insecticide but because of its high toxicity to fish it has been restricted. 

Aldrin, a chlorinated insecticide now banned for use in the United States, can be made by Diels-Alder reaction of hexachloro-l,3-cyclopentadiene with norbomadicne. What is the structure of aldrin ... 

Synonyms AI3-15558 BRN 0976722 C-56 Caswell No. 478 CCRIS 5919 EINECS 201-029-3 EPA pesticide chemical code 027502 Graphlox EICCP EICCPD EICPD Elex Elexachloro-1,3-cyclopentadiene l,2,3,4,5,5-Hexachloro-l,3-cyclopentadiene EIRS 1655 NC1-C55607 NSC 9235 PCCP PCL Perchloro-l,3-cyclopentadiene Perchlorocyclopentadiene RCRA waste number U130 UN 2646. 

The 3-acyl-2(3F/)-oxazolones function as good dienophiles in cycloaddition reactions with cyclic 2,4-dienes such as cyclopentadienes and anthracenes. Thus, the thermal reaction of 3-acetyl-2(37/)-oxazolone with cyclopentadiene and the hexachloro and hexamethyl derivatives gives endo-cycloadducts exclusively. In particular, the chiral cycloadducts 221 and 223 derived from the diastereoselective Diels-Alder reactions of 3-(2-exo-alkoxy-l-apocamphanecarbonyl)-2(3/7)-oxazo-lones with hexamethylcyclopentadiene and 9,10-dimethylanthracene, respectively, are highly useful as chiral 2-oxazolidinone auxiliaries. The conformationally rigid roofed structures play a crucial role in affording excellent chiral induction (Fig. 5.54). 

AI3-25719 Bichlorendo Caswell No. 411 CCRIS 413 CG-1283 Cyclopentadiene, hexachloro-, dimer 1,3-Cyclopentadiene, 1,2,3,4,5,5-hexachloro-, dimer Dechl-orane ... 

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