Thermally initiated reactions of allyl sec-butyl sulfone. Observation of a [1, 3]-allylic rearrangement

SO Myong, LW Linder Jr, SC Seike Jr…

Index: Myong, Sun Ok; Linder, Linus W.; Seike, Stephen C.; Little, R. Daniel Journal of Organic Chemistry, 1985 , vol. 50, # 13 p. 2244 - 2251

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Citation Number: 7

Abstract

Allyl alkyl sulfones undergo thermal rearrangement to afford alkenes and sulfur dioxide. Details of the mechanism were investigated by studying the thermolysis of allyl see-butyl sulfone (1). Gas-phase pyrolysis of 1 afforded propene, butenes, isopentane, l, &hexadiene, and 4-methyl-1-hexene (3) as major products. The activation energy for the process was determined to be 41.4 f 2.3 kcal/mol in the temperature range 220-272" C. As the ...