Index 199Dioxane, see 1,4-Dioxane
1,4-Dioxane 3, 150
Dioxirane 152
3,3-dimethyl-, reaction with phenanthrene 152
Dipolar cycloadditions 20
Dipole moment
of pyridine 5
of piperidine 5
of pyrrole 7
of pyrrolidine 7
Dipyrromethane, from pyrrole 82
Diquat 184
Direct arylation 30
Directed ortho metallation (DoM) 38
using amides 17
Divicine 192
DMAP, see 4-Dimethylaminopyridine
DMF, see N,N-Dimethylformamide
DMFDMA, see Dimethylformamide dimethyl acetal
DNA 48, 122, 163, 164
DNBF, see 4,6-Dinitro-2,1,3-benzoxadiazole
DoM, see Directed ortho metallation
Dopamine 169
Doping (electronic) 193
Double helix, hydrogen bonding 48
dppe, see Ethylenebis(diphenylphosphine)
dppf, see 1,1-Bis(diphenylphosphino)ferrocene
Drug names 167
Dyes, reactive 181
Eccoxolac 174
Electrofl uorescence 194
-Electrons 4
Electrophilic substitution, benzene 4
directing effect of substituents 11
mechanism 10
Enamines 18, 20, 95
Episulfi de, see Thiirane
Ergot fungus 165
Ergotamine 165, 192
Ergotism 192
Erlenmeyer azlactone 115
Eschenmoser’s salt 12
Esomeprazole ((S)-omeprazole) (Nexium) 167
Ethyl cyanoacetate, in ring synthesis of an
amino-pyrimidinone 59
Ethyl diazoacetate, in ring synthesis of a 1,2,4,5-tetrazine 142
Ethylene imine, see Aziridine
Ethylene oxide, see Oxirane
Ethylene sulfi de, see Thiirane
Ethylenebis(diphenylphosphine) (dppe) 22
5-Ethyloctanoic acid, from 2,5-dimethylthiophene-
3-CO(CH 2 ) 2 CO 2 H 102
Ethyne, synthetic equivalents in Diels–Alder reactions
135, 141
Etodolac (Eccoxolac) 174
F&F, see Flavours and Fragrances
FAD, see Flavin adenine dinucleotide
FADH 2 160
Famotidine (Pepcid) 170
FH 4 , see Tetrahydrofolic acid
Fipronil 183
ring synthesis of pyrazole 183
Fischer synthesis of indoles 94, 95
mechanism 95
Flagyl 176
Flavin adenine dinucleotide (FAD) 160, 161
Flavones 76
pigments 166
ring synthesis 77
Flavours and Fragrances 192
Flavylium, see 2-Phenyl-1-benzopyrylium
Flea drops 183
Flocoumafen 184
Fluconazole (Difl ucan) 176
Fluorescein 181
Fluorination, electrophilic 13
N-Fluoro-N-(phenylsulfonyl)benzenesulfonamide 13
5-Fluorouracil (5-FU) (Carac) 178
Folic acid 159, 176, 178
tetrahydro- 159
Formamidine, in ring synthesis of a pyrimidinone 59
Formica 181
Formylation, electrophilic 12
2-Formylbenzoic acid, in ring synthesis of phthalazinone 60
Friedel–Crafts reactions 14, 100, 102
Friedländer synthesis of quinolines 68
-D-Fructopyranose 154
-D-Fructopyranose 154
(5-FU) (Carac) 178
Furans
bromination 99, 100
2-bromo-, in Suzuki-Miyaura reaction 53
from furan 100
2-bromo-5-formyl-, in Suzuki-Miyaura reaction 113
2-bromo-5-methoxycarbonyl-, in Stille reaction 135
3-bromo-, in Sonogashira reaction 102
2-carboxylic acid, 5-(tetrazol-5-yl)-, from cross coupling 135
reaction with singlet oxygen 104
2,3-dibromo-, in Stille reaction 31
2,5-di-t-butyl-, oxidation to (E)-2,2,7,7-tetramethyloct-
4-ene-3,6-dione 103
ring synthesis 105
Diels–Alder reactions 19, 103, 104
2,5-dihydro-2,5-dimethoxy-, from furan 99, 100
2,5-dihydro-2-nitro-5-acetoxy-, from furan 99
2,5-dimethyl-3-ethoxycarbonyl-, ring synthesis 105
dipole moment 8
disconnections for ring synthesis 105
2-ethyl-4-methyl-, ring synthesis 105
2-ethyl-5-methyl-, oxidation to (Z)-hept-3-ene-2,5-dione
103
2-hydroxy, tautomerism 104
2-(1-hydroxyethyl)-, oxidation to
6-hydroxy-2-methyl-2H-pyran-3(6H)-one 103
2-iodo-, from 2-lithio- 101
2-lithio-, from 3-lithio- 101
from furan 17, 101
3-lithio-, from 3-bromo- 101
Mannich substitution 100
2-methyl-, reaction with HCl–MeOH 100
nitration 99
numbering 2, 99