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Note | Regular issue | Vol 81, No. 10, 2010, pp.2323-2334
Published online, 24th August, 2010
DOI: 10.3987/COM-10-11993
Ozonolyses of Isophorone and of 3-Methyl-2-cyclohexen-1-one and Subsequent Reactions of the Respective Ozonides to Afford Di-, Tri- and Tetraozonides

In Chan Jung,* Sad Alam Sheikh, Byong-Mun Jon, Wei Li, Bon-Suk Goo, and In-Soo Jeong

*Department of Chemistry, Hanseo University, Seosan 356-706, Korea

Abstract

Ozonolyses of isophorone (1a) and 3-methyl-2-cyclohexen-1-one (1b) in pentane, followed by treatment of the ozonolyses products with O-methyl- hydroxylamine afforded the ozonides 3,3,5-Trimethyl-6,7,8-trioxabicycle[3.2.1]octane-1-carbaldehyde-O-methyloxime (5a) and 5-Methyl-6,7,8-trioxabicyclo[3.2.1]octane-1-carbaldehyde-O-methyloxime (5b), respectively. Coozonolyses of ozonides 5 with selected carbonyl compounds resulted in the formation of diozonides (9, 11), triozonides (12) and tetraozonides (14).