Short path syntheses of α-diozonides by sequential ozonolyses of acetylenes and O-methyl oximes

Yuxiang Dong, Karl Griesbaum, Kevin J. McCullough

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Ozonolyses of but-2-yne 1 in the presence of added carbonyl compounds 3 afford a-oxo ozonides 4. Subsequent cycloadditions between ozonides 4 and cyclohexanone oxide 6, generated in situ by ozonolysis of O-methylcyclohexanone oxime, yield in turn a-diozonides 7 into which have been incorporated the carbon skeletons of all three substrates involved. Ozonolyses of acyloxy-substituted but-2-ynes 9 yield the corresponding bicyclic a-oxo ozonides 11 which subsequently participate in analogous cycloadditions with 6 to produce the corresponding a-diozonides 12. X-Ray crystallographic analysis of the crystalline diozonide 12a shows that it has been formed exclusively by exo-addition of 6 to 11a.

Original languageEnglish
Pages (from-to)1601-1604
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
Publication statusPublished - 7 Jun 1997

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