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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 1, Number 2
February 20, 1980 

Mechanism and Products During the Homolytic Addition of CCl4 and Cl3CBr to β-Halostyrenes
Sung Soo Kim
During the homolytic reactions of CCl4 or Cl3CBr with β-halo-styrenes, β-haloradicals are key intermediates. They are to be stabilized via three pathways; β-cleavage, halogen transfer and telomerization. The three reaction paths are delicately controlled by the energetics of their formation and stabilization. When the formation of a β-haloradical is accompanied by considerable excess of energy from an exothermic reaction, β -cleavage is often dominant over the halogen transfer. On the other hand, if the radical forms via a reversible reaction, two processes become competitive. β-Eliminated bromine atoms from β -bromoradicals generate Br2 via Cl3CBr + ·Br ↔ Br2 + ·CCl3·Br2 may act as a better scavenger than Cl3CBr for the β-bromoradicals. Differcnt reactivities of chlorine, bromine and trichloromethyl radicals towards olefinic pi-bond are clarified in terms of the beat content of the addition reactions.
45 - 49
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