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Kinetics of the thermal reaction of 1,1,2-trimethylcyclopropane

✍ Scribed by H. E. O'Neal; D. Henfling

Publisher
John Wiley and Sons
Year
1972
Tongue
English
Weight
415 KB
Volume
4
Category
Article
ISSN
0538-8066

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✦ Synopsis

The gas-phase reaction kinetics of 1,1,2-trimethylcyclopropane have been studied in First-order unimolecular rate constants for overthe temperature range of 70Cb755"K. all reactant disappearance fit the Arrhenius equation 61.08 f 0.51 log ko (sec-l) = 14.47e Reaction products and the relative rates of their formation are found to be reasonably consistent with the biradical mechanism.

Experimental

1 , 1,2-Trimethylcyclopropane was prepared by the Simmons-Smith reaction [ 11.

An equimolar mixture of 2-methyl-2-butene, diiodomethane, and Zn-Cu couple (0.76 mole) was refluxed for 24 hr at 40°C in anhydrous diethyl ether. Repeated distillation of the product, using a spinning-band column for the final distillation gave 3 ml of chromatographically pure 1,1,2-trimethylcyclopropane (bp (1 atm) 52.1-52.4"C).

The thermally induced kinetic studies were carried out in a 200-cc Pyrex reaction cell (dead space less than (O.2yO). This was suspended in a well-stirred air furnace. Temperature was controlled to better than f0.3"C using a Dormann Instruments 1300 control unit. GLC product analyses were made on a 20 ft X in. AgN03-benzyl cyanide 60/80 Chrom P column at O"C, using a Varian Aerograph 1500 hydrogen flame detector chromatograph and a Sargent Model T R recorder equipped with mechanical disc integrator. Samples of all possible CsHlz olefin products used in identification of reaction products by GLC retention time comparisons were obtained from K and K Laboratories.

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