LOW-TEMPERATURE HYDROBROMINATION OF ALLYL CHLORIDE AND AUTOWAVE REGIME OF A SOLID-STATE REACTION

Spontaneous hydrobromination of allyl chloride (AC) proceeds in the li quid phase (180-220 K, thermal effect DELTAH = 17 kcal mol-1) to give 1-chloro-2-bromopropane; active centres produced by radiolysis at 77 K at the glass transition (87-95 K) initiate a chain addition reaction of HBr to AC to form 1-chloro-3-bromopropane (thermal effect DELTAH = 13.2 kcal mol-1). This is the first example of hydrobromination at mat rix devitrification; a local brittle fracture of the irradiated sample of AC + HBr gives an autowave of chemical conversion spread over the sample.