Index 211Sheep dips 183
Sildenafi l (Viagra) 123, 175
Silicon substituents, removal with fl uoride 11
Singulair 168
Skatole, as perfume component 191
Skraup synthesis of quinolines 68
Socrates 165
Sodium dichloroisocyanurate 139
Sodium pentothal 55, 174
Sominex 170
Sonogashira reaction, examples 26, 27, 28, 31, 39, 74, 102,
128, 140
Sotolone 186
SPhos, see 2-Dicyclohexylphosphino-2,6-dimethoxybiphenyl
Stannane cross-couplings 25
Stannanes, from organolithium reagents 15, 16
Stannanes in cross-couplings, examples 10, 15, 16, 25, 38, 39,
51, 54, 80, 81, 91, 101, 112, 113, 121, 135, 141
Statins 175
Stille reaction, examples 25, 28, 31, 39, 54, 66, 81, 91, 113, 135
Strawberry furanone 186
Streptomyces anulatus 166
Strontium bis-(1-methyl-5-nitriminotetrazolate) 185
Strychnine 165, 169
Strychnos nux vomica 165
Sulfamethoxazole (Septrin) 176
Sulfi des from organolithium reagents 15, 16
Sulfolane 150
Sulfur, formation by decomposition of
5-phenyl-1,2,3,4-thiatriazole 138
Sulfurol 191
Sumatriptan (Imigran) 172
Suzuki–Miyaura reaction, examples 23, 24, 26, 29, 31, 32, 39,
53, 54, 66, 81, 91, 92, 102, 113, 135
Sydnones 137
Synthetic equivalents
of but-2-ene-1,4-dial 19, 99
of butane-1,4-dial 19, 99
of chloroethanal 117, 118
of malondialdehyde 46, 120
of N,N-diformylhydrazine 136
of phosgene 108
of 1,3-keto-aldehydes 18, 44
of 1,3-diketones 19, 44, 46
of ethyne, in Diels–Alder reactions 135, 141
Systemic herbicide 183
T, see Thymine
Tagamet 170
Tartrazine 115, 190
TBAF, see Tetra-n-butylammonium fl uoride
3-TC (Lamivudine) 177
TCNQ, see Tetracyanoquinodimethane
Tea 186
Telomestatin 166
Temodar 178
Temozolomide (Temodar) 139, 177, 178
2,2:6,2 -Terpyridine 44
2,3,5,6-Tetrachloro-1,4-benzoquinone, see Chloranil
Tetracyanoquinodimethane (TCNQ) 193, 194
1,1,3,3-Tetraethoxypropane, synthetic equivalent
of malondialdehyde 120
2,3,4,5-Tetrahydro-2,5-dimethoxyfuran, synthetic equivalent
of butane-1,4-dial 19, 99
Tetrahydrofuran (THF) 3, 150
Tetrahydropyran 3, 154
conformation 154
6,7,8,9-Tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one,
ring synthesis 61
Tetrakis(triphenylphosphine)palladium(0) 22
Te t r a -n-butylammonium fl uoride (TBAF) 11
1,2,3,4-Tetrahydrocarbazole, ring synthesis 94
Tetrathiafulvalene 193, 194
Tetrazene 185
1,2,3,4-Tetrazine 139
1,2,3,5-Tetrazine 139
1,2,4,5-Tetrazine 139
3,6-bis(methoxycarbonyl)-, Diels–Alder 141
ring synthesis 142
3,6-bismethylthio-, reaction with BocNH 2 –NaH 140
3,6-bis(pyridin-2-yl)-, ring synthesis 142
Diels–Alder with an alkyne 53
3-phenyl-, Diels–Alder 20
1 H-Tetrazole, tautomerism 132
2 H-Tetrazole, tautomerism 132
Tetrazoles
acidity 10
N-alkylation 133
5-amino- 185
basicity 132
5-bromo-1-benzyl-, in Suzuki–Miyaura reaction 13
5-bromo-1-methyl-, reaction with piperidine 133
5-carboxylic acid-1-methyl-, decarboxylation 134
5-carboxylic acid-2-methyl-, decarboxylation 134
5-cyano-, reaction with MeI 134
5-ethoxycarbonylmethyl-, ring synthesis 136
1-c-hexyl-5-methyl-, ring synthesis 136
5-lithio-1-benzyl-, from the tetrazole 135
5-lithio-1-methyl-, ring opening 135
1-methyl-, Mannich substitution 133
synthesis via decarboxylation of 5-acid 134
1-methyl-5-phenyl-, from 5-phenyltetrazole 135
2-methyl-, synthesis via decarboxylation of 5-acid 134
5-(4-methylphenyl)-, ring synthesis 136
5-nitro- 186
5-phenyl-, reaction with MeI 134
with t-BuOH–acid 135
5-thiol-1-methyl-, from 5-lithio- 135
5-tri-n-butylstannyl-2-Bom-, in Stille reaction 135
Tetrazolo[1,5-a]pyridine, ring opening to azide isomer 146
Tetronic acid 104
Theobromine 124, 186
Theophylline 124
THF, see Tetrahydrofuran
Thiadiazinones, Diels–Alder 139
Thiadiazoles
chloro-, nucleophilic substitution, relative reactivities 138
relative aromaticities 138
ring synthesis 138, 139
1,2,3-Thiadiazoles 137
5-chloro-4-phenyl-, reaction with PhLi at S with ring
opening 138
4-carboxylic acid, ring synthesis 139
4-lithio-, from the heterocycle 138