Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

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REFERENCES 731 93. Tartakovsky VA, Luk’yanov OA, Novikov SS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1966: 2186–2187 (2246–2247 russ.). 94. Chlenov IE, Sokolova IL, Novikov SS, Tartakovsky VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1973; 22: 460–461 (473 russ.). 95. Gree R, Carrie R. J. Am. Chem. Soc. 1977; 99: 6667–6672. 96. Seebach D, Lyapkalo IM, Dahinden R. Helv. Chim. Acta 1999; 82: 1829–1842. 97. Chlenov IE, Morozova NS, Khudak VI, Tartakovsky VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1970; 19: 2492–2494 (2641–2643 russ.). 98. Stepanova OR, Golod EL. J. Org. Chem. Russ. 1998; 34: 1246–1251 (1307–1310 russ.). 99. Denmark SE, Thorarensen A. Chem. Rev. 1996; 96: 139–143. 100. Denmark SE, Cottell JJ. The Chemistry of Heterocyclic Compounds, Vol. 59: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, John Wiley & Sons, 83–167, 2002. 101. Denmark SE, Moon Y-C, Cramer CJ, Dappen MS, Senanayake CBW. Tetrahedron 1990; 46: 7373–7392. 102. Amantini D, Fringuelli F, Pizzo F. J. Org. Chem. 2002; 67: 7238–7243. 103. Denmark SE, Kesler BS, Moon Y-C. J. Org. Chem. 1992; 57: 4912–4924. 104. Perekalin VV, Lipina ES, Berestovitskaja VM, Efremov DA. Nitroalkenes: Conjugated Nitro Compounds, John Wiley & Sons, New-York, 131–149, 1994. 105. Wade PA, Murray JK, Shah-Patel S, Carrol PJ. Tetrahedron Lett. 2002: 2585–2588. 106. Denmark SE, Cramer CJ, Sternberg JA. Tetrahedron Lett. 1986: 3693–3696. 107. Denmark SE, Cramer CJ, Sternberg JA. Helv. Chim. Acta 1986; 69: 1971–1989. 108. Denmark SE, Daffen Ms, Cramer CJ. J. Am. Chem. Soc. 1986; 108: 1306–1307. 109. Uno H, Goto K-I, Watanabe N, Suzuki H. J. Chem. Soc., Perkin Trans. 1 1989: 289–295. 110. Denmark SE, Moon Y-C, Senanayake CBW. J. Am. Chem. Soc. 1990; 112: 311–315. 111. Denmark SE, Stolle A, Dixon JA, Guagnano VA. J. Am. Chem. Soc. 1995; 117: 2100–2101. 112. Risaliti A, Forchiassini M, Valentin E. Tetrahedron 1968; 24: 1889–1898. 113. Felluda F, Nitti P, Pitacco G, Valentin E. Tetrahedron 1989; 45: 2099–2108. 114. Felluda F, Nitti P, Pitacco G, Valentin E. Tetrahedron 1989; 45: 5667–5678. 115. Nielsen AT, Archibald TG. Tetrahedron 1970; 26: 3475–3485. 116. Huffman JW, Cooper MH, Hiburo BB, Pennington WT. Tetrahedron 1992; 48: 8213–8228. 117. Chinchilla A, Backvall J-E. Tetrahedron Lett. 1992: 5641–5644. 118. Colonna FP, Valentin E, Pitacco G, Ricaliti A. Tetrahedron 1973; 29: 3011–3017. 119. Ferri RA, Pitacco G, Valentin E. Tetrahedron 1978; 34: 2537–2543. 120. Benedetti F, Pitacco G, Valentin E. Tetrahedron 1979; 35: 2293–2299. 121. Barabella G, Bruekker S, Pitacco G, Valentin E. Tetrahedron 1984; 40: 2441–2449. 122. Barabella G, Pitacco G, Russo C, Valentin E. Tetrahedron Lett. 1983; 24: 1621–1622. 123. Felluda F, Nitti P, Pitacco G, Valentin E. J. Chem. Soc., Perkin Trans. 1 1991: 1645–1652. 124. Pitacco G, Pizzioli A, Valentin E. Synthesis 1996: 242–248.
732 NITRONATES 125. Felluda F, Nitti P, Pitacco G, Valentin E. J. Chem. Soc., Perkin Trans. 1 1992: 2331–2336. 126. Miyashita M, Vanani T, Yoshikoshi A. J. Am. Chem. Soc. 1976; 98: 4679–4681. 127. Miyashita M, Vanani T. J. Am. Chem. Soc. 1984; 106: 2149–2156. 128. Miyashita M, Kumadzava T, Yoshikoshi A. Chem. Lett. 1980: 1043–1044. 129. Yoshikoshi A, Miyashita M. Acc. Chem. Res. 1985; 18: 284–290. 130. Seebach D, Brook HA. Helv. Chim. Acta 1985; 68: 319–324. 131. Brook HA, Seebach D. Can. J. Chem. 1987; 65: 836–850. 132. Marti RE, Heinzer J, Seebach D. Liebigs Ann. 1995: 1193–1216. 133. Scheeren H, Frissen AE. Synthesis 1983: 794–796. 134. Denmark SE, Senanayake BW, Ho GD. Tetrahedron 1990; 46: 4857–4876. 135. Denmark SE, Schnute ME. J. Org. Chem. 1991; 56: 6738–6739. 136. Denmark SE, Senanayake CBW. J. Org. Chem. 1993; 58: 1853–1858. 137. Denmark SE, Schnute ME. J. Org. Chem. 1994; 59: 4576–4595. 138. Denmark SE, Thorarensen A. J. Org. Chem. 1994; 59: 5672–5680. 139. Denmark SE, Marcin LR. J. Org. Chem. 1993; 58: 3857–3868. 140. Denmark SE, Marcin LR. J. Org. Chem. 1995; 60: 3221–3235. 141. Denmark SE, Schnute ME, Marcin LR, Thorarensen A. J. Org. Chem. 1995; 60: 3205–3220. 142. Denmark SE, Thorarensen A, Middleton DS. J. Org. Chem. 1995; 60: 3574–3575. 143. Tohda Y, Yamawaki N, Matsui H, Kawashima T, Ariga M, Mori Y. Bull. Chem. Soc. Jpn. 1988; 61: 461–466. 144. Tonda Y, Matsui H, Kawashima T. Bull. Chem. Soc. Jpn. 1993; 66: 1222. 145. Backvell JE, Karlsson U, Chinchilla R. Tetrahedron Lett. 1991: 5607–5610. 146. Barco A, Benetti S, Pollini GP, Spalluto G, Zanirato V. Tetrahedron Lett. 1991; 32: 2517–2520. 147. Papchikin A, Agback P, Plavec J, Chattopadhyaya J. J. Org. Chem. 1993; 58: 2874–2879. 148. Denmark SE, Guaguano V, Dixon JA, Stolle A, Marcin LR. J. Org. Chem. 1997; 62: 4610–4628. 149. Denmark SE, Marcin LR. J. Org. Chem. 1997; 62: 1675–1686. 150. Denmark SE, Dixon JA. J. Org. Chem. 1998; 63: 6178–6195. 151. Denmark SE, Hurd AR. J. Org. Chem. 2000; 65: 2875–2886. 152. Denmark SE, Martinborough EA. J. Am. Chem. Soc. 1999; 121: 3046–3056. 153. Tishkov AA, Lyapkalo IM, Kozincev AV, Ioffe SL, Strelenko YuA, Tartakovsky VA. Eur. J. Org. Chem. 2000: 3229–3233. 154. Smirnov VO, Tishkov AA, Ioffe SL, Zatonsky GV, Strelenko YuA, Smit WA. Mendeleev Commun. 2002: 117–118. 155. Brusa D, Felluda F, Nitti P, Pitacco G, Valentin E. Gaz. Chim. Ital. 1992; 122: 85–87. 156. Denmark SE, Homez L. Heterocycles 2002; 58: 129–136. 157. Avalos M, Babiano R, Ciutas P, Higes FJ, Jimenez JL, Palacios JI, Silia AA. J. Org. Chem. 1996; 61: 1880–1882.
Page 2:
NITRILE OXIDES, NITRONES, AND NITRO
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NITRILE OXIDES, NITRONES, AND NITRO
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CONTENTS Series Foreword vii List o
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LIST OF ABBREVIATIONS AIBN 2,2’-a
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LIST OF ABBREVIATIONS xi RC radical
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2 NITRILE OXIDES + − − + + −
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4 NITRILE OXIDES NaOHa1 R-CH=NOH Na
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6 NITRILE OXIDES ammonium nitrate (
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8 NITRILE OXIDES R O N N R′ N NO
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10 NITRILE OXIDES HON C(NO 2) Me Me
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12 NITRILE OXIDES which rapidly eli
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14 NITRILE OXIDES Dimethyl furoxan-
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16 NITRILE OXIDES R2P(O)C=NOH N(CH2
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18 NITRILE OXIDES obtained by the s
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20 NITRILE OXIDES (136, 137), appli
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22 NITRILE OXIDES RCNO + R′CH=CH2
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24 NITRILE OXIDES aldehydes are bei
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26 NITRILE OXIDES R Cr(CO)3 Ar = 3,
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28 NITRILE OXIDES bonding effect. T
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30 NITRILE OXIDES Selective nitrile
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32 NITRILE OXIDES H H H RCNO + R =
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34 NITRILE OXIDES O O O Br ArCNO Ar
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36 NITRILE OXIDES the bridgehead po
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38 NITRILE OXIDES O O OR′ H H 94
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40 NITRILE OXIDES H O N H O O R 101
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42 NITRILE OXIDES O O 111 CH(OMe)2
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44 NITRILE OXIDES Ph2CHCO N H2C N M
Page 61 and 62:
46 NITRILE OXIDES O (Me 2CHO) 2P N
Page 63 and 64:
48 NITRILE OXIDES R 137a-f PhCNO N
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50 NITRILE OXIDES R N Ph N O O Ph R
Page 67 and 68:
52 NITRILE OXIDES derivatives 4-R 2
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54 NITRILE OXIDES OH N H (CH2)n R N
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56 NITRILE OXIDES Ar R 1 N 174 N O
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58 NITRILE OXIDES N-benzyladamantyl
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60 NITRILE OXIDES Ph3P L Rh O 194 N
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62 NITRILE OXIDES and modern prepar
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64 NITRILE OXIDES R 2 = MeO2C, R 3
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66 NITRILE OXIDES 223 with 2-iodoni
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68 NITRILE OXIDES N O O N N N R R R
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70 NITRILE OXIDES complexes [PdCl2(
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72 NITRILE OXIDES measured for the
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74 NITRILE OXIDES Oxidation of (alk
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76 NITRILE OXIDES electrophiles as
Page 93 and 94:
78 NITRILE OXIDES O 2N Ph R S N ONC
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80 NITRILE OXIDES PhCH 2Co(dmgH) 2p
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82 NITRILE OXIDES are formed exclus
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84 NITRILE OXIDES On treatment with
Page 101 and 102:
86 NITRILE OXIDES PhSO 2 R R′C=NO
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88 NITRILE OXIDES R X = OTMS O O H
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90 NITRILE OXIDES TBSO H Me NOH TBS
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92 NITRILE OXIDES A synthetic appro
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94 NITRILE OXIDES N O H CO 2Me H 2N
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96 NITRILE OXIDES the unambiguous a
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98 NITRILE OXIDES t-Bu t-Bu O O O O
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100 NITRILE OXIDES COX-2 selectivit
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102 NITRILE OXIDES elastase release
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104 NITRILE OXIDES ambient temperat
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106 NITRILE OXIDES HO Ph O N O O N
Page 123 and 124:
108 NITRILE OXIDES and acceptor sub
Page 125 and 126:
110 NITRILE OXIDES 31. Belen’kii
Page 127 and 128:
112 NITRILE OXIDES 87. Matt Ch, Gis
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114 NITRILE OXIDES 146. Faita G, Pa
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116 NITRILE OXIDES 208. Gravestock
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118 NITRILE OXIDES 266. Tian L, Xu
Page 135 and 136:
120 NITRILE OXIDES 324. Stajer G, B
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122 NITRILE OXIDES 382. Himo F, Lov
Page 139 and 140:
124 NITRILE OXIDES 445. Yamamoto T,
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126 NITRILE OXIDES 504. D’ Alelio
Page 144 and 145:
2 Nitrones: Novel Strategies in Syn
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SYNTHESIS OF NITRONES 131 Treated w
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R H OH R N R Oxone K2CO3 OH R N O S
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H N H RO R N H N H CO2H OH O OR P O
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R1 − − R N O 1-CH2-NH-R2 2 BF4
Page 154 and 155:
O N+ O − (EtO) 2P XCH2CN (X = Cl,
Page 156 and 157:
Et H3CO H 3CO − O R R N 1 H N H O
Page 158 and 159:
[O] SYNTHESIS OF NITRONES 143 N H N
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(R 1 O)m O 47 ( )n OH + RNHOH (R 1
Page 162 and 163:
R 5 R 6 R 5 R 6 R6 R5 O R 1 R5 R R6
Page 164 and 165:
+ N O − (EtO)2(O)P HO (EtO)2(O)P
Page 166 and 167:
H O − N O 166, 167 AZN O N − +
Page 168 and 169:
AcO OAc OAc O OAc O OAc OAc O OAc O
Page 170 and 171:
SYNTHESIS OF NITRONES 155 Similarly
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O Ph Et 2N R R 1 S CHO N COOEt R =
Page 174 and 175:
SYNTHESIS OF NITRONES 159 In a simi
Page 176 and 177:
SYNTHESIS OF NITRONES 161 (EtO) 2(O
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R 2 R 1 Cl Ph O · Cl Ph N OR Ph N
Page 180 and 181:
R 1 NO2 R 2 PhSeH R 1 (EtO)2(O)PCH2
Page 182 and 183:
HO MeO2C Br "N-exo" O O O MeO2C 105
Page 184 and 185:
R O N H Ar * SeOTF CH 2Cl 2 R O N H
Page 186 and 187:
SYNTHESIS OF NITRONES 171 (where R
Page 188 and 189:
2 PhCH = NONa H 150 N OH + R 1 R 2
Page 190 and 191:
R 2 R 3 H R 1 R 1 R 2 N O + N OH 16
Page 192 and 193:
R 1 R 2 − O + N OOH R 1 R 2 O OMe
Page 194 and 195:
[R1R2C(NO2)] − + M R3 178 175 (R
Page 196 and 197:
R R R R 188 189 NHOH a: R = Me b: R
Page 198 and 199:
STRUCTURE AND SPECTRA OF NITRONES 1
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R R H C N O + H 3C Bu t + C STRUCTU
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I R 1 − O R 2 ( )n − ( )n N O
Page 204 and 205:
Bu t Ph O N OH − + H H H CF 3 Ph
Page 206 and 207:
Bu N t H O + + N N − − ROCCH2 O
Page 208 and 209:
STRUCTURE AND SPECTRA OF NITRONES 1
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ELECTROCHEMICAL PROPERTIES AND EPR-
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R 2 R 1 N O ELECTROCHEMICAL PROPERT
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Page 218 and 219:
NITRONE COMPLEXES 203 radiolysis in
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R 2 226a-c R 1 N O + O N − + −
Page 222 and 223:
R 2 R O C N 1 R2 R3 + R 1 , R 2 , R
Page 224 and 225:
OH _ O + N R 1 a: R 1 = Me, b: R 1
Page 226 and 227:
R Me Me Me Me H N H 259 O O 255a-c
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NITRONE REACTIONS 213 2.6.2. Reduct
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N + O − • + ClO 2 N O • H O C
Page 232 and 233:
H O + N DMPO H O N N 228-232 MeOH P
Page 234 and 235:
Ph H3CO H3CO Ph N O 276 N O 281 O
Page 236 and 237:
Ph N O N F • Ph + Ph F Ph R F Ph
Page 238 and 239:
Ph Ph O O + N O − 286 Rl,Et 3B be
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Table 2.9 Electroreductive coupling
Page 242 and 243:
NITRONE REACTIONS 227 This reaction
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295a Br I NaOH, MeOH NaOH, MeOH NaO
Page 246 and 247:
H 3C R H3C N O − + O N CH3 CH 3 C
Page 248 and 249:
H + O N B− − − − H N − BH
Page 250 and 251:
H H X + O N H RLi O N E X = CH2, NC
Page 252 and 253:
NITRONE REACTIONS 237 Nucleophilic
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O BnO Ph Et 2N O BnO H 317 O O HO N
Page 256 and 257:
NH 2 NH 2 Boc N H2N N(OH)Bn Boc N P
Page 258 and 259:
NITRONE REACTIONS 243 EtAlCl2, TiCl
Page 260 and 261:
NITRONE REACTIONS 245 Addition of v
Page 262 and 263:
HO R R R HO N Bn NHBoc NH 2 NHBoc N
Page 264 and 265:
RCHO BocNHOH R 2 + + O N R1 − PhS
Page 266 and 267:
BzlOOC + NH3 Cl i OH BzlO Cl Cl Bzl
Page 268 and 269:
Table 2.12 Addition a of 2-lithiofu
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H 2N O BnO O OH O CO2H H2N O N H OH
Page 272 and 273:
353 b a BnO BnO 354 Bn N CHO OBn b
Page 274 and 275:
Table 2.13 Addition of organolithiu
Page 276 and 277:
R N O Cl 367 −O + N Bu t LDA, THF
Page 278 and 279:
HO HO OH N N • Ph • O OH O HO P
Page 280 and 281:
RO2C N O X • N O • N O N O •
Page 282 and 283:
N O 373 N O a 374, 376, 377 R2 376
Page 284 and 285:
+ N O − HN HO O R1 S R2 R3 + Ph 1
Page 286 and 287:
+ R 1 N R2 O O R 1 N R 2 − R 1 R
Page 288 and 289:
NITRONE REACTIONS 273 Table 2.14 Sy
Page 290 and 291:
+ Ph N O − Bn + O Et 3SiO MeO O H
Page 292 and 293:
O O O N Pri OCOPh R Me Bn CO 2H NHC
Page 294 and 295:
N O OBu t N O THF,−78°C, 1 h OBu
Page 296 and 297:
O O O O 292 O H N −O + Bn O HO N
Page 298 and 299:
NITRONE REACTIONS 283 The reaction
Page 300 and 301:
O − O O BnO O O + O − O − N P
Page 302 and 303:
R 1 R 2 NH 2 COOH Br a: b: c: d: e:
Page 304 and 305:
NITRONE REACTIONS 289 2.6.6.1.11. N
Page 306 and 307:
NITRONE REACTIONS 291 Nucleophilic
Page 308 and 309:
O − O O + NBoc− O NBoc N Bn 1.
Page 310 and 311:
NITRONE APPLICATION IN RADICAL POLY
Page 312 and 313:
REACTIONS OF DIPOLAR 1,3-CYCLOADDIT
Page 314 and 315:
Page 316 and 317:
Page 318 and 319:
a b c d REACTIONS OF DIPOLAR 1,3-CY
Page 320 and 321:
R REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 322 and 323:
Page 324 and 325:
a REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 326 and 327:
Page 328 and 329:
− REACTIONS OF DIPOLAR 1,3-CYCLOA
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Page 332 and 333:
Page 334 and 335:
Page 336 and 337:
Page 338 and 339:
Page 340 and 341:
Page 342 and 343:
Page 344 and 345:
Page 346 and 347:
(a) REACTIONS OF DIPOLAR 1,3-CYCLOA
Page 348 and 349:
O HO REACTIONS OF DIPOLAR 1,3-CYCLO
Page 350 and 351:
Page 352 and 353:
Bn REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 354 and 355:
Page 356 and 357:
CO 2Me O O REACTIONS OF DIPOLAR 1,3
Page 358 and 359:
Page 360 and 361:
Page 362 and 363:
Page 364 and 365:
H H REACTIONS OF DIPOLAR 1,3-CYCLOA
Page 366 and 367:
Page 368 and 369:
Page 370 and 371:
Page 372 and 373:
Page 374 and 375:
Me REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 376 and 377:
Page 378 and 379:
Page 380 and 381:
Page 382 and 383:
O REACTIONS OF DIPOLAR 1,3-CYCLOADD
Page 384 and 385:
Page 386 and 387:
Page 388 and 389:
Ph Ph REACTIONS OF DIPOLAR 1,3-CYCL
Page 390 and 391:
− O Me REACTIONS OF DIPOLAR 1,3-C
Page 392 and 393:
Page 394 and 395:
Page 396 and 397:
Ph REACTIONS OF DIPOLAR 1,3-CYCLOAD
Page 398 and 399:
Page 400 and 401:
B C A Closed [5,6] adduct B B KINUG
Page 402 and 403:
KINUGASA REACTION ([2 + 2] CYCLOADD
Page 404 and 405:
O O N N N O R R O O L 1 : N N N 1 m
Page 406 and 407:
R 1 R 1 O + N 774 a-e Δ O N N Ph 1
Page 408 and 409:
783 784 + N O + CH3 − N O Ph CH3
Page 410 and 411:
R 1 NHOH 793 + R 2 CHO 794 Hydroxyl
Page 412 and 413:
REACTIONS WITH CYCLOPROPANES 397 O
Page 414 and 415:
REFERENCES 399 properties and synth
Page 416 and 417:
REFERENCES 401 (d) Mottley C, Mason
Page 418 and 419:
REFERENCES 403 46. Sankuratri N, Ja
Page 420 and 421:
REFERENCES 405 105. Saladino R, Ner
Page 422 and 423:
REFERENCES 407 159. Sridharan V, Mu
Page 424 and 425:
REFERENCES 409 205. Cupone G, De Ni
Page 426 and 427:
REFERENCES 411 259. Balasundaram B,
Page 428 and 429:
REFERENCES 413 310. (a) Cicchi S, M
Page 430 and 431:
REFERENCES 415 (b) Creary X. Acc. C
Page 432 and 433:
REFERENCES 417 410. Dziembowska T,
Page 434 and 435:
REFERENCES 419 459. Bourquet E, Ban
Page 436 and 437:
REFERENCES 421 Papers of 6-th Inter
Page 438 and 439:
REFERENCES 423 573. Ok D, Fisher MH
Page 440 and 441:
REFERENCES 425 636. (a) Jost S, Gim
Page 442 and 443:
REFERENCES 427 690. Haire DL, Janze
Page 444 and 445:
REFERENCES 429 721. Manzoni L, Aros
Page 446 and 447:
REFERENCES 431 762. Baldwin JE, Adl
Page 448 and 449:
REFERENCES 433 808. Leggio A, Liguo
Page 450 and 451:
3 Nitronates SEMA L. IOFFE N. D. Ze
Page 452 and 453:
SYNTHESIS OF NITRONATES 437 as O-nu
Page 454 and 455:
SYNTHESIS OF NITRONATES 439 These r
Page 456 and 457:
SYNTHESIS OF NITRONATES 441 It shou
Page 458 and 459:
X-C(NO 2) 3 NO 2-C(NO 2) 3 R R′ C
Page 460 and 461:
R R′ X NO 2 base −H + R R′ X
Page 462 and 463:
Br NaNO 2/DMF Cl R 6 R=C6H5; CO2MeR
Page 464 and 465:
OH NO 2 R EtO2CN NCO 2Et PPh 3, ben
Page 466 and 467:
NO 2 O Me R 2 R 1 PhSH Et 3N cat. M
Page 468 and 469:
R R O OAc 19 Mn III −H + NO2 Me M
Page 470 and 471:
Ag[ArC(NO2)2] 26 heptane 100°, 50
Page 472 and 473:
NO2CH=C(NO2)Ph [RR′CN 2 28 RR′C
Page 474 and 475:
Me O 2N Me O 2N 29a Br EtO 2CC CCO
Page 476 and 477:
SYNTHESIS OF NITRONATES 461 (39) (s
Page 478 and 479:
SYNTHESIS OF NITRONATES 463 In the
Page 480 and 481:
R 1 R R 2 NO 2 + R 5 R 3 42 43 R 6
Page 482 and 483:
O O N R + R"CO NO2 R′ N 42 43c Ph
Page 484 and 485:
SYNTHESIS OF NITRONATES 469 3.2.2.3
Page 486 and 487:
R R′ C R H C R′ NO2 [RR′C(NO2
Page 488 and 489:
Table 3.1 The silylation of AN by E
Page 490 and 491:
SYNTHESIS OF NITRONATES 475 Table 3
Page 492 and 493:
O Me 2RSi NMe 2 + − Me2N=C—OSiM
Page 494 and 495:
SYNTHESIS OF NITRONATES 479 decompo
Page 496 and 497:
A G N R O N H O O A Si R 1 RR 1 C=N
Page 498 and 499:
NO2CH2CH2CH2CO2ME Me CO2Me NO2CH CH
Page 500 and 501:
SYNTHESIS OF NITRONATES 485 than 20
Page 502 and 503:
R 1 R 2 LDA THF, −78°C R 1 O OLi
Page 504 and 505:
O R 1 N 51o-t OSiMe2R 3 R 2 PRINCIP
Page 506 and 507:
MeO2C H PRINCIPAL PHYSICOCHEMICAL D
Page 508 and 509:
PRINCIPAL PHYSICOCHEMICAL DATA AND
Page 510 and 511:
R' R PRINCIPAL PHYSICOCHEMICAL DATA
Page 512 and 513:
Table 3.8 (continued) PRINCIPAL PHY
Page 514 and 515:
Page 516 and 517:
Page 518 and 519:
Page 520 and 521:
Page 522 and 523:
Page 524 and 525:
Page 526 and 527:
Page 528 and 529:
** NO2 O O N O * N SiMe3 O PRINCIPA
Page 530 and 531:
Page 532 and 533:
XO R 1 N O H XO O N R R 2 = H R 3 X
Page 534 and 535:
EtO 2CCH N(O)OMe Δ or HCl NH3 / Me
Page 536 and 537:
R 1 R 2 OSi N O E—Nu R 1 R 2 REAC
Page 538 and 539:
O OM R′ N 113 R′′ Me 3SiX −
Page 540 and 541:
O O R 1 R 1 N N OSi R 2 OSi R 2 + M
Page 542 and 543:
R 1 PhO2S R 1 PhO 2S N NO2 O OSiMe
Page 544 and 545:
R 3 R 1 O R 4 R 3 R 3 R 1 R 1 55%-7
Page 546 and 547:
RR′C N MeOCO MeO C O OBEt 2 N O O
Page 548 and 549:
REACTIVITY OF NITRONATES 533 Yields
Page 550 and 551:
RO R 4 R 3 R 2 O N R 1 O P(OAlk) 3
Page 552 and 553:
REACTIVITY OF NITRONATES 537 Second
Page 554 and 555:
MeO2C Ph CO2Me O N O X 1 X 2 Ph H R
Page 556 and 557:
R CO2Me TiCl 4 reflux, overnight N
Page 558 and 559:
Me NO2 + Ph Me NO 2 Ph + Bu n O Bu
Page 560 and 561:
R R O2N O2N O N Regioselectivity +
Page 562 and 563:
REACTIVITY OF NITRONATES 547 Ref.33
Page 564 and 565:
REACTIVITY OF NITRONATES 549 Ref.52
Page 566 and 567:
MeO2C MeO 2C 160 N O OMe R OMgBr r.
Page 568 and 569:
R N O N O R N O N O Y Z X xylene, r
Page 570 and 571:
REACTIVITY OF NITRONATES 555 O N O
Page 572 and 573:
RCH2NO2 RHC N RHC N O OH Ac 2O/AcON
Page 574 and 575:
PhCOCH2SCHR′R′′ 180 R′R′
Page 576 and 577:
REACTIVITY OF NITRONATES 561 Both o
Page 578 and 579:
R 185 + R′ 195 NO2 OH ( )n KH; TH
Page 580 and 581:
NaNO2 AcOH 199 200 (+) -citronellen
Page 582 and 583:
O X X X X S 208 D F E SiMe3 NO 2 O
Page 584 and 585:
R′ R′′ HO R O N 213 O ClSi R
Page 586 and 587:
R SiO R AlkO N N R′′ O + R′
Page 588 and 589:
R′ R′ R′ R′ O N OSi 229 OH
Page 590 and 591:
R′′ OH Si - Me2Bu t Si R′ R N
Page 592 and 593:
R = Me R′ = Ph(86%);CO2Me(28%) O
Page 594 and 595:
R′O HO OR′ R′′ R′ O N * *
Page 596 and 597:
REACTIVITY OF NITRONATES 581 orient
Page 598 and 599:
REACTIVITY OF NITRONATES 583 isomer
Page 600 and 601:
O N O 249a-g + R′ 250a,b R O N O
Page 602 and 603:
REACTIVITY OF NITRONATES 587 Experi
Page 604 and 605:
BuO R 1 Me Me Me Et Et Et Me * ** O
Page 606 and 607:
REACTIVITY OF NITRONATES 591 3.4.4.
Page 608 and 609:
N N OH HO H H H HO (−)-hastinecin
Page 610 and 611:
REACTIVITY OF NITRONATES 595 compli
Page 612 and 613:
Four component [4+2] [4+2] [4+2] do
Page 614 and 615:
Bn O O REACTIVITY OF NITRONATES 599
Page 616 and 617:
Me2Si R 1 NO2 R 1 R 2 R 2 291 O EtO
Page 618 and 619:
O 2N R * = EtO + 296 OEt R * OAc Et
Page 620 and 621:
G * OH G * O G * OH: 305 306 OH Ph
Page 622 and 623:
SILYLATION OF NITRO COMPOUNDS AS A
Page 624 and 625:
RCH2CH2CHNO2 319 H a B − BH + SIL
Page 626 and 627:
R 1 R 2 Ph R2 R1 O N OSi NO2 R2 R1
Page 628 and 629:
Page 630 and 631:
Me 2N CH 2 N OSiMe 3 R 1 R 2 + O N
Page 632 and 633:
Ref.459 Ar Ar HF 2 − HF 2 − + N
Page 634 and 635:
R 2 R 3 R 1 NO 2 SiX/Et3N (1) SILYL
Page 636 and 637:
NO 2 NO2 SiX/Et 3N NO 2 Me 3SiCl/DB
Page 638 and 639:
Page 640 and 641:
Page 642 and 643:
C N OH OH C N OH + + OH B Si - trio
Page 644 and 645:
R 2 R3 R4 R 1 O N TfOH O 348f-h R 2
Page 646 and 647:
Page 648 and 649:
R O N OX SILYLATION OF NITRO COMPOU
Page 650 and 651:
Page 652 and 653:
Pheq O N O 356a TfOTBS Pheq O N 357
Page 654 and 655:
(a) SiO O N 6 Nu (b) N N (c) SiO Si
Page 656 and 657:
Page 658 and 659:
Page 660 and 661:
Page 662 and 663:
# N CO2Me OSi OMe SiO N CO2Me OSi S
Page 664 and 665:
Page 666 and 667:
( ) 3 H Ph O N OMe 391a H N Ph O N
Page 668 and 669:
R 2 R 3 R 4 R 2 R 3 R 4 R 2 An O N
Page 670 and 671:
R = CO2Me; NO2;Δ t > 50°C (O 2N)2
Page 672 and 673:
X NO 2 SILYLATION OF NITRO COMPOUND
Page 674 and 675:
Page 676 and 677:
Page 678 and 679:
Page 680 and 681:
Page 682 and 683:
O N An 431(C) OTMS SILYLATION OF NI
Page 684 and 685:
R 1 432 R 1 434 E OR 3 NO2 R 2 N(OS
Page 686 and 687:
X R 1 434 R 2 R 1 432 X + A NO 2 R
Page 688 and 689:
Si - trialkylsilyl N OSi O Si SILYL
Page 690 and 691:
R 1 R 2 441 R 1 R 2 NO2 C NO 2 −
Page 692 and 693:
Page 694 and 695:
R 2 SILYLATION OF NITRO COMPOUNDS A
Page 696 and 697: SILYLATION OF NITRO COMPOUNDS AS A
Page 698 and 699: NH 3 N H * + H 2C CO 2Et R 1 = H or
Page 700 and 701: N N N N R 1 =Me, R 2 =H 92% Bz Me N
Page 704 and 705: RN(NO2)SiMe3 RN N + 473a,b OSiMe3 i
Page 708 and 709: Cl N OSiMe3 MeO OSiMe3 Me 476d SILY
Page 710 and 711: R R 495 NO2 493 N(OTBS)2 R′I (Me3
Page 712 and 713: R 1 N(OSi)2 Nu: (b) R 2 EX (a) Si =
Page 716 and 717: Me Me Me Me Me Me Ph eq O 507a Ph N
Page 720 and 721: R 3 R 4 R 5 R 3 R 4 R 5 Et3N R 3 R
Page 722 and 723: R3 R2 R 4 NO2 O R 1 R 1 O N 521 R 2
Page 724 and 725: X R 2 R 1 NO2 ii For 528a iii For 5
Page 726 and 727: MeO2C MeO2C MeO2C 528a BSA 530a O N
Page 736 and 737: Me 3SiO Me3SiO N Me3SiON Me 3Si H N
Page 740 and 741: CONCLUSION 725 those containing fun
Page 742 and 743: REFERENCES 727 Due to the silylatio
Page 744 and 745: REFERENCES 729 35. Tartakovsky VA,
Page 748 and 749: REFERENCES 733 158. University of I
Page 750 and 751: REFERENCES 735 221. Kornilov VI, Pa
Page 752 and 753: REFERENCES 737 273. Shitkin VM, Iof
Page 754 and 755: REFERENCES 739 329. Harada K, Shimo
Page 756 and 757: REFERENCES 741 382. Tartakovsky VA,
Page 758 and 759: REFERENCES 743 437. Kim BH, Curran
Page 760 and 761: REFERENCES 745 491. Ioffe SL, Lyapk
Page 762: REFERENCES 747 540. Gilchrist TL, R
Page 765 and 766: 750 INDEX 1,3-Dipolar cycloaddition
Page 767 and 768: 752 INDEX Nitrone reactions (contd.
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Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

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