The Nitro group in organic sysnthesis - Feuer

370 SUBJECT INDEX

Nitronium tetrafluoroborate, 9, 13, 15, 16 Nitroolefination, 100 (S)-5-Nitropentan-2-ol, 108 1-Nitro-2-phenylsulfonylethylene, 102, 217,

334

1-Nitro-2-phenylthioethylene, 76, 357

3-Nitropiperidines, 353

1-Nitropropane, 37, 55, 77, 106, 109, 127, 149, 153

2-Nitropropane, 86, 104, 106, 107, 110, 115, 117, 118, 133, 134, 136, 148, 188, 183, 220, 222, 191, 216

1-Nitro-1-propene, 39, 74, 75, 78, 87, 89, 91, 92, 93, 326

2-Nitro-1-propene, 39, 89, 93, 95, 100 3-Nitropyridine, 356

2-Nitropyrrole, 313

3-Nitropyrrole, 240, 329

β-Nitrostyrene, 44, 74, 75, 77, 86, 91, 93, 94, 96, 97, 98, 99, 113, 168, 170, 176, 177, 327, 328, 352

Nitro sugars, synthesis, 24, 48–51, 137 α-Nitro sulfides, 150, 212, 213

β-Nitro sulfides, 71–73, 79, 212, 213, 216 α-Nitro sulfones

β-Nitro sulfones, 217 β-Nitro sulfoxides, 102 Pd-catalyzed allylation, 141 preparation, 150

SRN1 reaction, 134 Nitrothiazoles, 135 Norslanadione, synthesis, 206

Nucleophilic aromatic displacement (SNAr), 302

of o-dinitrobenzene, 303

of p-dinitrobenzene, 302, 303, 308 Nucleophilic aromatic substitution of

hydrogen (NASH), 309 m-chloronitrobenzene, 315, 318 o-chloronitrobenzene, 311 p-chloronitrobenzene, 311, 315 m-dinitrobenzene, 313, 314, 317 m-fluoronitrobenzene, 313 3-nitroaniline, 319

nitrobenzene, 309, 311, 312, 314, 318 2-nitrofurans, 313

4-nitroimidazole, 315

2-nitropyrroles, 313

6-nitroquinoline, 321

2-nitrothiophene, 312, 315

3-nitrothiophene, 312

Nucleosides, synthesis, 205, 210

Octaethylporphyrin, 337 Organometallic reagents

addition to nitroalkenes, 95–99 1-Oxabuta-1,3-diene, 235 Oxidation to nitro compounds

of amines 20–22 of isocyanates 25

of β-nitro alcohol to α-nitro ketone, 46 of oximes, 21–23

with OXONE, 23

with m-perbenzoic acid (m-CPBA), 21 with peroxytrifluoroacetic acid, 21

Oximes, reduction of nitro compounds, 176–177

Paar-Knorr reaction, pyrrole synthesis, 110, 325–326

Pancratistatin, 218

(+)-Paraherquamide B, synthesis, 345 Pd(0) catalysis, see allylation of nitro

compounds

Penicillaric acids, synthesis, 81 Phenanthridines, 355

Phenylacetone, synthesis from nitroalkenes, 165

1-Phenylheptane-1,5-dione, synthesis, 201 Phenylisocyanate, generation of nitrile

oxides, 167–168 Phenylnitromethane, 18 Phenylthiomethyl isocyanide, 315 1-(Phenylthio)-nitroalkenes, 81–83 Phenylthionitrometane, 80 Pheromone, synthesis, 35, 48, 331

Phosphazene base, pyrrole synthesis, 335 Phytochromobilin, synthesis, 332–333 Polyoxin C, synthesis, 81 Porphobilinogen, synthesis, 332 Porphyrins, synthesis, 337

Polypyrroles, 336

Proazaphosphatrane, base for nitro aldol reaction, 37

L-Proline, asymmetric Michael addition, 118

(–)-Psudophymaminol, synthesis, 101 Pyrazoles, synthesis, 358 Pyrazolo[3,4-b]pyridine, synthesis, 242

(–)-Pyrenophorin, synthesis, 108 Pyridinium chlorochromate (PCC), 46 Pyrimidines, synthesis, 345

Pyrroles, synthesis, 177, 325–338

Pyrrolidines, synthesis, 277, 347–351 Pyrrolidin-2-ones, synthesis, 90, 352 Pyrrolines, synthesis, 347 Pyrrolizidines, synthesis, 350 Pyrrolo[2, 1-c][1, 4]benzodiazepine,

synthesis, 356 Pyrrolo[2,3-d]pyrimidines, synthesis, 345 Pyrrolostatin, synthesis, 331

Pummerer rearrangement, 222

Radical reaction addition, 209 cyclization, 210 elimination, 214–218

substitution, 133–138, see SRN1 Recifeiolide, synthesis, 139 Retro Diels-Alder reaction, 334 D-Ribo-nitro-aldol, synthesis, 50

Ring cleavage of cyclic α-nitro ketones (retro Henry reaction), 131–133

(–)-Rosmarinecine, synthesis, 288

Scandium triflate, 109

Secondary nitro group, denitration, 197

(+)-Sedridine, synthesis, 252 Selenation

nitroalkanes, synthesis of nitroalkenes, 153

nitroalkenes, Michael addition, 74

Silver nitrite, synthesis of nitro compounds, 17

Silyl nitronates,

1,3-dipolar cycloaddition, 75, 268–273 nitro aldol reaction, 54–55

SmI2, reduction of nitro compounds, 175 Sm(Oi-Pr)3, 328

Sodium nitrite, Nef reaction, 163

nitration of alkyl halides, 18–19 Sodium perborate, 21

Sodium salt of methylmercaptan, Sodium sulfide, 215

SN1 reaction of nitro compounds, deoxy nitro sugars, 154, 190 allylic nitro compounds, 187 SN2 reaction of nitro compounds

Lewis acid assistance, α-nitro sulfides, β-nitro sulfides, 189–191

Intramolecular reaction, 191–192 Spiro ketals, pheromones, synthesis, 131,

166

SUBJECT INDEX 371

SRN1 reaction, 133–136, 154, 182–185 alkyl mercury halides, 136

deoxy nitro sugars, 185 geminal dinitro compounds, 134 geminal halonitroalkanes, 134 Kornblum reaction, 184

α-nitro nitriles, 184 p-nitrobenzyl halides, 133 tertiary nitro compounds, 184

SRN2, 137

Staurosporine, synthesis, 352 Stereoselective reaction

nitro aldol reaction, 51

(–)-Strychnine, synthesis, 308 β-Sulfonyl nitroalkenes, 217 Sundberg indole synthesis, 342

Tandem [4 + 2]/[3 + 2] cycloaddition, 279–295

(+)-australine, synthesis, 290

(+)-castanospermine, synthesis, 290

(+)-casuarine, synthesis, 283

(+)-crotanesine, synthesis, 289 3,4-disubstituted pyrrolidines, cis and

trans, 277

(+)-7-epiaustraline, synthesis, 282

(–)-hastanecine, synthesis, 280

(+)-macronecine, synthesis, 281 Tandem Michael addition, 92, 114 Taxane, synthesis, 201

Tethered reaction, 260 Tetrabutylammonium fluoride (TBAF), 52,

80–81, 104–106 Tetradecano-14-lactone, synthesis, 202

(+)-13-Tetradodecanolide, synthesis, 202 Tetramethylguanidine (TMG)

for nitro-aldol, 32, 36

for Michael addition, 103–105, 117 Tetranitromethane, nitration, 5, 16 D-Threonine, synthesis, 83

Tosylmethyl isocyanide (TosMIC), pyrrole synthesis, 328–330

2-Tosylpyrrole, synthesis, 332 Trialkylborane, alkyl radical precursor, 97,

138, 308

Tributyltin hydride (Bu3SnH), radical denitration, 109, 111–113,

193–211, 216–218

indole synthesis (Fukuyama reaction), 344 Triethylsilane, ionic hydrogenation, 213 Trifluoroacetyl nitrate, nitration, 16

372 SUBJECT INDEX

Trimethylsilyl iodide, 169 1,3,5-Trinitrobenzene, indole synthesis, 346 2,4,6-Trinitrotoluene, indole synthesis, 342 Triton B, Michael addition, 109 Trovafloxacin, synthesis, 151

Tuberine, synthesis, 79

Ultrasound irradiation, 41 α,β-Unsaturated carbonyl compounds,

synthesis, 88, 147, 167, 222, 224–225, 260

α,β-Unsaturated nitriles, 224 α,β-Unsaturated sulfones, pyrrole synthesis,

336

Urea-hydrogen peroxide (UHP), oxidation of amines or oximes, 21

Vancomycin, synthesis, 306

Vicarious nucleophilic substitution (VNS), 309–318

Vicinal dinitro compounds, radical elimination, 214–215

Ytterbium triflate, Michael addition, 106

Zirconium tetra tert-butoxide, oxidation of amines, 21

Zinc reagents, Michael addition, 97–99