6533b85dfe1ef96bd12be710

RESEARCH PRODUCT

Isomerization of perchlorohexatriene in three consecutive rearrangements to perchloro-2-vinylbutadiene

Dieter SchollmeyerHeiner Detert

subject

010405 organic chemistryStereochemistryChemistryOrganic ChemistryDrug Discovery010402 general chemistry01 natural sciencesBiochemistryMedicinal chemistryPyrolysisIsomerization0104 chemical sciences

description

Perchlorohexatriene isomerizes in three subsequent rearrangements to perchloro-2-vinylbutadiene. A radical-induced Z-E-equilibration of linear perchlorohexatrienes is followed by cyclization to a methylenecyclopentene. Under flash-vacuum pyrolysis conditions, a ring contraction to 1,2-dimethylenecyclobutane occurs. In the condensed phase, a radical-induced ring opening generates the branched perchloro-vinylbutadiene. All compounds are converted to hexachlorobenzene, but only at very high temperatures.

https://doi.org/10.1016/j.tetlet.2017.01.040