Weygand/Hilgetag Preparative Organic Chemistry

Contents
Introduction; Organization of the Material 1
PART A. Reactions on the Intact Carbon Skeleton 3
Chapter L Formation of carbon-hydrogen bonds 5
1.1. Formation of the carbon-hydrogen bond by addition 5
I. Addition of hydrogen to C=C bonds and aromatic systems 5
1. Chemical reducing agents 5
a. Reduction by non-noble metals 6
i, Reduction by sodium and alcohols 6
ii, Reduction with sodium amalgam 7
iii, Reduction with aluminum amalgam 8
iv, Reduction by solutions of alkali or alkaline-earth metals in liquid ammonia
8
v, Reduction by lithium in organic amines 10
vi, Reduction by zinc, tin, or aluminum 11
b. Electrolytic reduction 12
c. Reduction by lithium aluminum hydride or similar compounds 13
d. Reduction by diimine 15
e. Other reducing agents 17
2. Catalytic hydrogenation 18
a. Catalysts 18
i, Noble-metal catalysts (Adams catalysts) 19
ii, Skeletal alloy catalysts (Raney metals) 22
iii, Metal catalysts 24
iv, Copper oxide-chromium oxide catalysts (Adkins catalysts) 26
v, Sulfide catalysts 27
b. Apparatus and procedure for hydrogenation 28
i, Hydrogenation on a shaking machine 28
ii, High-pressure hydrogenation 30
iii, Hydrogenation in a catalyst tube 31
c. Examples of catalytic hydrogenation 32
i, Choice of catalyst 32
ii, Hydrogenation of olefinic double bonds 32
iii, Selective hydrogenation 33
iv, Hydrogenation of aromatic compounds 36
v, Hydrogenation of heterocycles 38
vi, Catalytic hydrogenation by bonded hydrogen 40
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