The Journal of Organic Chemistry

Characterization of intermediates in the reaction of ozone with di-tert-butylacetylene. A novel pivaloylating system

JA Jenkins, GD Mendenhall

Index: Jenkins, Jerry A.; Mendenhall, G. David Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 3997 - 4000

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Citation Number: 2

Abstract

Reaction of di-tert-butylacetylene (la) with ozone in<-40 OC aprotic solvents upon warming leads to pivalic anhydride, pivalil, and pivalic acid, with evolution of isobutane, isobutene, carbon dioxide, and carbon monoxide. Spectral and chemical evidence indicated the presence of at least two labile intermediateg in the reaction. Ozonolysis of the alkyne in the presence of compounds containing a hydroxyl function led to their pivaloyl derivatives with ...

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