Characterization of Intermediates in the Reaction of Ozone with Di-tert-butylacetylene. A Novel Pivaloylating System
Document Type
Article
Publication Date
1-1-1981
Abstract
Reaction of di-tert-butylacetylene (1a) with ozone in < -40 °C 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 intermediates in the reaction. Ozonolysis of the alkyne in the presence of compounds containing a hydroxyl function led to their pivaloyl derivatives with incorporation of both tert-butyl groups, probably via fragmentation of an adduct of ROH to an intermediate carbonyl oxide. © 1981, American Chemical Society. All rights reserved.
Publication Title
Journal of Organic Chemistry
Recommended Citation
Jenkins, J.,
&
Mendenhall, G.
(1981).
Characterization of Intermediates in the Reaction of Ozone with Di-tert-butylacetylene. A Novel Pivaloylating System.
Journal of Organic Chemistry,
46(20), 3997-4000.
http://doi.org/10.1021/jo00333a012
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/8063