Weygand/Hilgetag Preparative Organic Chemistry

Contents xxiii
3. Ketene from acetone 1031
4. Cleavage of cyclohexene derivatives 1032
5. Conversion of lumisterol into tachysterol 1032
1.2. Oxidative cleavage of carbon-carbon bonds 1033
I. Oxidative cleavage of C—C bonds in alkenes and cycloalkanes 1033
1. Manufacture of fatty acids for soaps by the Fischer-Tropsch-Gatsch process 1033
2. Oxidation of cyclohexane to adipic acid by nitric acid 1033
II. Oxidative degradation of side chains on aromatic and heterocyclic rings 1034
1. Oxidative degradation of long aliphatic chains in aromatic or heterocyclic
systems 1034
2. Degradation of phenol homologs to phenolic carboxylic acids by an oxidative
alkali melt 1035
III. Oxidative degradation of olefins 1035
1. Oxidative cleavage of unsaturated carbonyl compounds by alkali melts 1036
2. Oxidative cleavage of olefins to aldehydes by the usual oxidants 1037
3. Oxidative cleavage of olefins to ketones and carboxylic acids by the usual
oxidants 1037
4. Oxidative cleavage of olefins by ozone 1038
5. Wieland degradation of side chains 1039
IV. Oxidative cleavage of carbon-carbon bonds where a functional group is at the
position of cleavage 1040
1. Oxidative cleavage of secondary alcohols and ketones 1040
2. Oxidative cleavage of methyl ketones 1041
3. Cleavage by lead tetraacetate 1043
V. Oxidative degradation of aromatic and heterocyclic ring systems 1045
1. Oxidative cleavage of fused aromatic ring systems 1045
2. Oxidative cleavage of fused heterocyclic ring systems 1045
3. Fumaric acid from furfuraldehyde 1046
1.3. Hydrolytic cleavage 1046
1. Fencholic acid from fenchone 1046
2. Acid fission of /?-diketones and /?-oxy esters 1047
PART D. Rearrangements of carbon compounds 1053
1.1. Rearrangements with retention of the carbon skeleton 1054
I. Migration of a multiple bond 1054
1. Migration of a double bond 1054
2. Allylic rearrangement 1056
3. Migration of a triple bond 1058
II. Rearrangement with change of an oxygen group 1058
1. Conversion of epoxides into carbonyl compounds 1058
2. Willgerodt reaction 1059
3. Keto-enol tautomerism 1060
4. Isomerization of ketols (acyloins) 1061
5. Cannizzaro rearrangement 1062
6. Acyl-lactone rearrangement 1063
7. Other rearrangements 1063
III. Rearrangement of nitrogen compounds 1064
1. Amadori rearrangement 1064
2. Chapman rearrangement 1064
3. Rearrangement of amine oxides 1065
4. Neber rearrangement 1065