212 Index
1,2,4-Thiadiazole 137
1,2,5-Thiadiazole 137
ring synthesis 139
1,3,4-Thiadiazole 137
ring synthesis 139
Thiamethoxam 182
Thiamin, see Vitamin B 1
1,2,3,4-Thiatriazole, controlled decomposition 138
stability 138
2-Thiazolone, 4-bromination 110
tautomerism 115
Thiazoles
2-amino-, diazotisation 116
ring synthesis 117
2-bromo-, in Stille reaction 25
basicity 10, 107
5-boronic acid pinacol ester, 2-trimethylsilyl-, from
5-lithio- 113
in Suzuki–Miyaura reaction 113
5-bromo-, in cross coupling with CO–EtOH 26
2-chloro-, reaction with phenylthiolate 110
from 2-amino- 116
2,4-dibromo-, from thiazol-2,4-dione 115
2,5-dibromo-, in Stille reaction 113
2,4-dimethyl-, ring synthesis 117
2,4-dione, reaction with POBr 3 115
disconnections for ring synthesis 116
2-formyl hydrazone, reaction with NiO 2 148
2-hydroxy-, tautomerism 115
2-lithio-, from 2-bromo- 113
2-hydroxy-aldehyde synthesis 114
2-lithio-4-bromo-, from 2,4-dibromothiazole 112
4-lithio-2-trimethylsilyl-, from 4-bromo- 112
5-lithio-2-trimethylsilyl-, from 2-trimethylsilyl- 10, 113
2-methyl-, nitration 109
4-methoxycarbonyl-, 2-substituted 118
numbering 2
ring synthesis by dehydrogenation of tetrahydro- 118
2-tri-n-butylstannyl-, in Stille reaction 113
2-trimethylsilyl-, from 2-lithio- 113
2-trimethylsilyl-4-bromo-, from 2-lithio- 112
4-trimethylstannyl-, from 2-trimethylsilyl-4-
trimethylstannylthiazole 112
5-trimethylstannyl-, 10
Thiazolium ylides 113
in thiamin activity 161, 162
Thiazolium, reduction 114
3-methyl-, iodide 107
1,2,3-Thiazolo[3,2-c][1,2,3]triazole, lithiation 148
ring synthesis 148
Thietane 3, 153
ring synthesis 155
2 H-Thiete 3
Thiiranes 3, 150
2,2-dimethyl-, reaction with piperidine 151
2,3-dimethyl-, reaction with P(OEt) 3 and ring
opening 152
from oxiranes 156, 157
anS,S-dioxide, elimination of SO 2 152
ring opening with nucleophiles 151
Thioacetamide, in ring synthesis of thiazoles 117
Thionation of ketones 105
Thiopentone (as sodium salt) (Sodium Pentothal) 173
Thiophenes
2-boronic acid, cross coupling with ene-phosphate 102
3-boronic acid, from 3-lithio- 101
in Suzuki–Miyaura reaction 102
3-boronic acid-4-formyl-, in Suzuki–Miyaura reaction 24
bromination 99
2-/5-bromo-, reductive removal 99
2-bromo-, copper-catalysed N-substitution with 30
Grignard 101
in Stille reaction 91
in Suzuki–Miyaura reaction 102
N-heteroarylation of imidazole 111
2-bromo-3-iodo-, in Sonogashira reaction 31
3-bromo-, in nickel(0)-catalysed Kumada–Corriu
reaction 25
3-bromo-2-formyl-, from 2-lithio-3-bromo- 101
3-bromo-2-iodo-5-methyl-, in Sonogashira reaction 26
2-t-butoxy-, from 2-Grignard 101
2-carbonyl chloride, in Stille reaction 25
dipole moment 8
3,5-di-t-butyl-, S,S-dioxygenation 103
3,5-di-t-butyl- S,S-dioxide, Diels–Alder 103
2,5-diethyl-, ring synthesis 106
2,3-diiodo-, in Sonogashira reaction 31
disconnections for ring synthesis 105
2,5-di(trimethylsilyl)- S-oxide, Diels–Alder reaction 104
2,5-di(trimethylsilyl)- S-oxidation 104
2-formyl-, from thiophene 100
Friedel–Crafts acylations 100, 102
2-hydroxy, from 2-t-butoxythiophene 101
tautomerism 101
2-lithio-, reaction with N-tosylaziridine 101
2-lithio-3-bromo-, from 3-bromo- 101
3-lithio-, from 3-bromo- 101
Mannich substitution 100
2-methyl-5-phenyl-, ring synthesis 105
natural 162
nitration 99
numbering 2, 99
reaction with succinic anhydride 100
reduction/hydrogenolysis 102
resonance energy 8
structure 8
tetrahydro- 1,1-dioxide, see Sulfolane
3-tri-n-butylstannyl-, in Stille reaction 113
from 3-lithio- 101
Vilsmeier reaction 100
Thiourea
in ring synthesis of 2-aminothiazoles 117
of a pyrimidine thione 58, 59
Thymidine 48
Thymine (T) 48, 164
Timolol (Timoptic) 173
Timoptic 173
TIPS-indole, see Indole, 1-tri-isopropyl-
TIPS-pyrrole, see Pyrrole, 1-tri-isopropyl-
Titanium, low valent 96
TNT 185
p-Toluenesulfi nic acid/-sulfi nate, leaving group 84, 118
Topoisomerase I 178
TosMIC, see Tosylmethyl isocyanide