3424-05-3

Usage

InChI:InChI=1/C6Cl8/c7-2-3(8)6(13,14)1(4(9)10)5(2,11)12

Upstream product

• 56-23-5 tetrachloromethane 
• 21400-41-9 1,1,2,4,4-pentachloro-1,3-butadiene 
• 7446-70-0 aluminium trichloride 
• 846550-69-4 3H,4H,5H-heptachloro-pent-1-ene 
• 6928-60-5 1,1,2,3,4,5,6,6-octachloro-hexa-1,3,5-triene 

Downstream Products

• 56-23-5 tetrachloromethane 
• 706-78-5 octachlorocyclopentene 
• 17218-59-6 2,3,4,4-tetrachloro-5-dichloromethylene-cyclopent-2-enone 
• 18964-31-3 2,3-dichloro-5-dichloromethylene-2-cyclopentene-1,4-dione 
• 118-74-1 hexachlorobenzene 
• 7782-50-5 chlorine 
• 87-82-1 hexabromobenzene 
• 1128-20-7 1,2-dichloro-3,4-bis-(dichloromethylene)cyclobut-1-ene 
• 3229-28-5 4,5-dichloro-4-cyclopentene-1,3-dione 

Relevant academic research and scientific papers

Thermal rearrangements of perchlorohexatrienes-structures and experimental and theoretical evaluation of pathways to isomerization and cyclization

We have prepared trans- (1) and cis-octachloro-1,3,5-hexatriene (2) by known routes and studied their thermal behavior experimentally and theoretically by ab initio calculations. The three double bonds in 1 and 2 are completely decoupled due to steric hindrance by the eight Cls, as indicated by calculations as well as the single-crystal X-ray structure of 1. The cis isomer 2 can be isomerized to the trans isomer 1 by heating it to 220-250 °C either neat or dissolved in highboiling solvents, leading to a roughly 2:1 mixture of trans and cis isomers. Calculations at several different levels of theory predict 1 and 2 to be isoenergetic within 2 kJmol-1. Unimolecular cis/trans isomerization is predicted to occur through an unusual vinylcyclobutene intermediate 7, whose formation faces a barrier of more than 150 kJmol -1, but whose stability is comparable to that of 1 and 2. The isomerization rate is strongly enhanced by the addition of small amounts of Br2 or Cl2 or by 3 and can be explained by a radical-induced isomerization mechanism. The heating of trienes 1 and 2 to 250 °C leads to cyclization, yielding 71% of the cyclopentene isomer 3. Compound 3 can be dechlorinated by treatment with copper powder to give fulvene derivative 4. Using flash vacuum pyrolysis, the thermal conversion of trienes 1 and 2 to hexachlorobenzene (5) occurs at higher temperatures between 600-1000 °C, likely via perchlorinated 1,3-cyclohexadiene (6) as an intermediate. The elimination of molecular Cl2 from 3 and 6 requires very high activitation energies in agreement with calculations. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

CONDENSATION OF 2-H-PENTACHLORO-1,3-BUTADIENE WITH CARBON TETRACHLORIDE IN THE PRESENCE OF ALUMINUM CHLORIDE

During the condensation of 2-H-pentachloro-1,3-butadiene with carbon tetrachloride in the presence of anhydrous aluminum chloride 2-trichloromethyl-1,1,3,4,4-pentachloro-1,3-butadiene, octachlorocyclopentene, and 1,2,3,3,5,5-hexachloro-4-(dichloromethylene)cyclopentene are formed as the main products.A possible mechanism for their formation is proposed.It was established that the C2 atom in th 2-H-pentachloro-1,3-butadiene molecule is the most favorable for attack by the trichloromethyl cation.