Cydohexene ozonolysis

The most common procedure is ozonolysis at -78 °C (P.S. Bailey, 1978) in methanol or methylene chloride in the presence of dimethyl sulfide or pyridine, which reduce the intermediate ozonides to aldehydes. Unsubstituted cydohexene derivatives give 1,6-dialdehydes, enol ethers or esters yield carboxylic acid derivatives. Oxygen-substituted C—C bonds in cyclohexene derivatives, which may also be obtained by Birch reduction of alkoxyarenes (see p. 103f.), are often more rapidly oxidized than non-substituted bonds (E.J. Corey, 1968 D G. Stork, 1968 A,B). Catechol derivatives may also be directly cleaved to afford conjugated hexa-dienedioic acid derivatives (R.B. Woodward, 1963). Highly regioselective cleavage of the more electron-rich double bond is achieved in the ozonization of dienes (W. KnOll, 1975). 

Problem 9,20 Predict the ozonolysis products of (a) cydohexene (b) 1-methyl-cyclopentene (c) 3-nieth>lcycloi entenc (d) 1,3-cyclohexadiene (e) 1,4-cyclohexa-diene. 

Problem 9.21 Both cydohexene and 1,7-octadiene yield the di-aldehyde OHC(CH2)4010 upon ozonolysis. What other facts would enable you to distinguish between the two compounds ... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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