Ozonolysis of bicyclic 1,2-dioxines: Initial scope and mechanistic insights
Date
2012
Authors
Cain, N.
Tiekink, E.
Taylor, D.
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Journal article
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Journal of Organic Chemistry, 2012; 77(8):3808-3819
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Nicole M. Cain, Edward R. T. Tiekink, and Dennis K. Taylor
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Abstract
The ozonolysis of bicyclic 1,2-dioxines was investigated using a variety of 1,4-disubstituted 1,2-dioxines along with a 1,3-dialkyl and steroidal example, with yields ranging from moderate to excellent. Two different pathways were observed upon reaction of the 1,4-disubstituted 1,2-dioxines with ozone; one pathway saw the "expected" results, that is, cleavage of the olefinic moiety with generation of 1,4-dicarbonyl 1,2-dioxines, while the other pathway revealed a previously unobserved rearrangement involving cleavage of the peroxide linkage along with loss of either CO or CO(2). Several unsymmetrical ozonolyses were also performed to further investigate the origins of this rearrangement, and initial mechanistic insights into the fragmentation pathways are discussed.
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Copyright © 2012 American Chemical Society