Page 343 - Arrow Pushing in Inorganic Chemistry A Logical Approach to the Chemistry of the Main Group Elements

INDEX 323
enamines, 3, 26–7 Dess–Martin periodinane (DMP), 288–90
enediolate, 56 electrophilic fluorinating agents, 264–8
Ene reaction, 37, 243–4 elemental halogens, 254–8
enolates, 3, 26–7, 181, 265–6, 268, 284–5 halate, acid-induced comproportionation of,
ethyl diazoacetate, 148 260–261
equilibrium constant, 5 halide, acid-induced comproportionation of,
260–261
fluoride donors and acceptors, 302–3 heptavalent chlorine, 271–5
fluoroantimonic acid, 194–5, 274 hypervalent organoiodine compounds, 283–4
formal charge (FC), 40–41 hypofluorous acid (HOF), 261–4
Friedel–Crafts reactions, 68 interhalogen compounds, 275–6
3
frustrated Lewis acid–base pairs (FLPs), 19, 61–3, -iodanes, 284–8
5
124 -iodanes, 288–90
dihydrogen activation by, 61–3 2-iodoxybenzoic acid (IBX), 288–90
molecular halogens, alkali-induced
gallium arsenide, 79–80 disproportionation of, 258–60
gallium nitride, 79–80 N-fluoro compounds, 264–8
gasotransmitter, 154, 203 in organic synthesis, 276–83
germylenes (Ge), 115–17 periodic acid oxidations, 290–291
glucokinase, 164 haloform reaction, 281–2
glycol cleavage by lead tetraacetate, 124–7 halonium ions, 23, 276–7
gold-xenon complexes, 316 hard acids, 8–9
green chemistry, 195–200 hard and soft Lewis acids and bases (HSAB) concept,
Grieco-Sharpless elimination, 246–7 8–9, 48, 130, 158, 163, 211, 293
Grignard reagents, 59–60 qualitative listing, 8
group 13 elements, 66–94 hard bases, 8–9
from borazine to gallium arsenide, 13–15 heavier pnictogens, 156–200
boryl anion, 87–88 Arbuzov reaction, 175–6
compounds, 76–80 arsenic toxicity, 168–71
group 13-based reducing agents, 73–6 arsenic-based DNA, 166–8
hydroboration, 70–72 biological signaling, 154, 203
indium-mediated allylations, 88–9 biomethylation, 168–71
as Lewis acids, 67–70 bismuth in organic synthesis, 195–200
low oxidation-state compounds, 80–86 Corey–Winter olefination, 185–6
thallium reagents, 89–94 halides, 160–163
group 14 elements, 96–128 hypophosphorous acid, disproportionation of,
alkene analogs, 115–20 173–5
alkyne analogs, 120–121 Mitsunobu reaction, 188–91
carbene, 115–20 oxides, 158–60
glycol cleavage by lead tetraacetate, 124–7 oxohalides, 160–163
hydrostannolysis, 113 phosphazenes, 180–184
organostannanes, 112–13 phosphorus, 163–6
Peterson olefination, 103–4 phosphorus ylides, 176–80
polystannanes, 113–15 SbF , 193–5
5
silanes, 104–6 superacids, 193–4, 200, 274
-silicon effect, allylsilanes, 106–9 Vilsmeier–Haack reaction, 191–3
silyl anions, 109–12 Wittig reaction, 176–80
silyl cations, 122–4 heptavalent chlorine, 271–5
silyl protecting groups, 98–103 heterolysis, 35
group 16 elements, 202–51, See also chalcogens higher-valent states, 215–18
higher-valent sulfur fluorides, 234–6
halate, acid-induced comproportionation of, 260–261 sulfur tetrafluoride (SF ), 234
4
halides, 160–163 Hofmann degradation, 282–3
acid-induced comproportionation of, 260–261 homolysis, 35
halogens, 252–99 Horner–Wadsworth–Emmons reaction, 176, 179
3
aryl- -bromanes, 294–8 Hünig’s base, 15, 181
bromine trifluoride, 291–4 hydrazine, synthesis of, 133–5