Reaction of the chloroallyl radical with molecular chlorine

Martens, G.; Godfroid, M.; Ramoisy, L.

doi:10.1039/p29720000200

Cited by 3 publications

(2 citation statements)

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“…The radical coupling products show preferential coupling with the least substituted end of the 1,1,2-trichloroallyl radical. Similar selectivity in radical coupling is also observed in reactions of alkyl radicals with alkyl-substituted allyl radicals (Martens et al, 1972;Baulch et al, 19(79).…”

Section: Resultssupporting

confidence: 60%

Pyrolysis of triallate

Johnson¹,

DeLane²

1987

J. Agric. Food Chem.

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Section: Resultssupporting

confidence: 60%

Pyrolysis of triallate

Johnson¹,

DeLane²

1987

J. Agric. Food Chem.

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“…Table LV). The major side product, propylene, can be formed by disproportionation of both allyl chloride and 1 -chloro-1 -propene: [15] have studied the chlorination of allyl chloride and/or I-chloro-I-propene. It has been found that the ratio of the concentrations of 1,3-dichloropropene and 3,3-dichloropropene is about 1 I:], over the temperature range 350-570°C, indicating that either CH2-CH=CHCl (I) is ten times more reactive than CHo=CH-CHCI (II), or that the canonical form I is closer to the actual structure of the chloroallyl radical than form 11.…”

Section: Discussionmentioning

confidence: 99%

Kinetics of the I₂‐catalyzed isomerization of allyl chloride to cis‐ and trans‐1‐chloro‐1‐propene. The stabilization energy of the chloroallyl radical

Alfassi

Golden

Benson

1973

Int J of Chemical Kinetics

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The I 2-catalyzed isomerization of allyl chloride to cis-and tmns-1 -chloro-l-propene was measured in a static system in the temperature range 225-329°C. Propylene was found as a side product, mainly at thr lower temperatures. The rate constant for an abstraction of a hydrogen atom from allyl chloride by an iodine atom was found to obey the equationUsing this activation energy together with 1 rt 1 kcal/mole for the activation energy for the reaction of H I with alkyl radicals gives DHO (CH2CHCHCI-H) = 88.6 =t 1.1 kcal/mole, and 7.4 i 1.5 kcal/mole as the stabilization energy (SE) of the chloroallyl radical. Using the results of Abell and Adolf on allyl fluoride and allyl bromide, we conclude DHO (CHZCHCHF-H) = 88.6 f 1.1 and DH" (CHtCHCHBr-H) = 89.4 =k 1.1 kcal/ mole; the SE of the corresponding radicals are 7.4 i 2.2 and 7.8 i 1.5 kcal/mole. The bond dissociation energies of the C-H bonds in the allyl halides are similar to that of propene, while the SE values are about 2 kcal/mole less than in the allyl radical, resulting perhaps more from the stabilization of alkyl radicals by a-halogen atoms than from differences in the unsaturated systems.

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