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

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Pheq O N O 356a TfOTBS Pheq O N 357a OTBS TBS – SiMe 2Bu t SILYLATION OF NITRO COMPOUNDS AS A PROCESS 637 OSi Ph (Si – TBS, SiMe 3) –30 ° C, TfOSi (10%–20% mol) Ph N –94 ° C, 0.5 h, TBSOTf (1 eq) SnBu 3 –70 ° → –30 ° C, 1 h, TBSOTf (1 eq) OTBS –78 ° , TBSOTf (1 eq) –30 ° –40 ° , TBSOTf (0.3 eq) Bn TBS N TBSO N Ph Ph TfOTBS, 0° OTBS 366 367 Scheme 3.210 Pheq O N 359a,b OSi O Pheq O N 361 OTBS Pheq O N OTBS 362 Pheq O N 363 Bz N Ph OTBS Ph O 91% dr 100:12:1 (at −78 ° C) 74% dr 100:26:1 40%–50% 60% (via (360)) O N 360 OTBS Pheq N Ph OTf− + 51% Pheq O 364 N OTBS O 60% 3 stereoisomeres 83%
638 NITRONATES For example, carbonyl derivatives (359a,b) can be prepared by the reaction of cation (357a) or by other triorganosilyl analogs with silyl enolates derived from acetophenone. Target nitroso acetal (359) can also be synthesized through the intermediate iminium salt (360) by C,C-coupling of cation (357a) with 1-phenyl- 1-N -pyrrolidinylethylene. Among other C,C-coupling reactions shown in Scheme 3.210, the reaction of cation (357a) with diene (366) can be noted, which occurs regioselectively at the terminal C,C double bond. The reaction of nitronate (356a) with N-silylenamine (367) is of particular interest. This process also occurs stereoselectively but by N,C-coupling. It should be noted that the resulting product (363) has the amino group and the trialkylsiloxy fragment in trans conÞguration. Detailed conÞgurational and conformational analyses of the starting sixmembered cyclic nitronates (356) of cationic intermediates (357), and C,Ccoupling products (357 + Nu), taking into account slow nitrogen inversion (IN) in nitroso acetals (see Section 3.4.3.4.4), made it possible to propose a mechanistic model based on the stereochemical outcome of the C,C-coupling process (Chart 3.23). Evidently, the stereoselectivity of the process is determined by the preference of the distal approach of the nucleophile (Nu) to the C-6 atom in the predominant conformation of cation (357) (Chart 3.23, a). In the resulting nitroso acetal, the nitrogen lone pair and the Nu ′ fragment are in a trans conÞguration. It should be noted that exactly the same stereochemical outcome can be obtained after the proximal approach of the nucleophile (Nu) to the C-6 atom in the minor conformation of cation (357 ′ ) (Chart 3.23, a). However, this seems to be unlikely for a number of reasons. First, the inversion of cations (357) has a high barrier (see Scheme 3.204, cation (349a)), and two conformers can be independently observed in the temperature range, where their C,C-coupling generally occurs. Second, the diastereomers ratio in C,C-coupling products of cation (349) with silyl ketene acetal exactly corresponds to the conformers ratio for this cation (349a:349a ′ ), that is, it is evident that the interaction occurs through the distal approach of silyl ketene acetal to the C-6 atom of observed conformations a and a ′ of the above mentioned cation. Finally, calculations demonstrated (162) that the distal approach of dipolarophiles to the C-6 atom of the dipole is also preferable in [3 + 2]-cycloaddition reactions of six-membered cyclic nitronates. The trans conÞguration of the nitrogen lone pair and the Nu ′ fragment in nitroso acetals can be attributed to the anomeric effect of this pair (see Chart 3.23, b). The most surprising fact is that the N,C-coupling reaction (356a→363) leads to a change in the mutual orientation of the respective Nu ′ fragment and the nitrogen lone pair. Evidently, conclusions cannot be drawn based on only one example. However, it can be hypothesized that the stereocontrol of this process
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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
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46 NITRILE OXIDES O (Me 2CHO) 2P N
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48 NITRILE OXIDES R 137a-f PhCNO N
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50 NITRILE OXIDES R N Ph N O O Ph R
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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
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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
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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
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108 NITRILE OXIDES and acceptor sub
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110 NITRILE OXIDES 31. Belen’kii
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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
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120 NITRILE OXIDES 324. Stajer G, B
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122 NITRILE OXIDES 382. Himo F, Lov
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124 NITRILE OXIDES 445. Yamamoto T,
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126 NITRILE OXIDES 504. D’ Alelio
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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
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O N+ O − (EtO) 2P XCH2CN (X = Cl,
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Et H3CO H 3CO − O R R N 1 H N H O
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[O] SYNTHESIS OF NITRONES 143 N H N
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(R 1 O)m O 47 ( )n OH + RNHOH (R 1
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R 5 R 6 R 5 R 6 R6 R5 O R 1 R5 R R6
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+ N O − (EtO)2(O)P HO (EtO)2(O)P
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H O − N O 166, 167 AZN O N − +
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AcO OAc OAc O OAc O OAc OAc O OAc O
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SYNTHESIS OF NITRONES 155 Similarly
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O Ph Et 2N R R 1 S CHO N COOEt R =
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SYNTHESIS OF NITRONES 159 In a simi
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SYNTHESIS OF NITRONES 161 (EtO) 2(O
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R 2 R 1 Cl Ph O · Cl Ph N OR Ph N
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R 1 NO2 R 2 PhSeH R 1 (EtO)2(O)PCH2
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HO MeO2C Br "N-exo" O O O MeO2C 105
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R O N H Ar * SeOTF CH 2Cl 2 R O N H
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SYNTHESIS OF NITRONES 171 (where R
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2 PhCH = NONa H 150 N OH + R 1 R 2
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R 2 R 3 H R 1 R 1 R 2 N O + N OH 16
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R 1 R 2 − O + N OOH R 1 R 2 O OMe
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[R1R2C(NO2)] − + M R3 178 175 (R
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R R R R 188 189 NHOH a: R = Me b: R
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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
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Bu t Ph O N OH − + H H H CF 3 Ph
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Bu N t H O + + N N − − ROCCH2 O
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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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NITRONE COMPLEXES 203 radiolysis in
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R 2 226a-c R 1 N O + O N − + −
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R 2 R O C N 1 R2 R3 + R 1 , R 2 , R
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OH _ O + N R 1 a: R 1 = Me, b: R 1
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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
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H O + N DMPO H O N N 228-232 MeOH P
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Ph H3CO H3CO Ph N O 276 N O 281 O
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Ph N O N F • Ph + Ph F Ph R F Ph
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Ph Ph O O + N O − 286 Rl,Et 3B be
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Table 2.9 Electroreductive coupling
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NITRONE REACTIONS 227 This reaction
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295a Br I NaOH, MeOH NaOH, MeOH NaO
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H 3C R H3C N O − + O N CH3 CH 3 C
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H + O N B− − − − H N − BH
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H H X + O N H RLi O N E X = CH2, NC
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NITRONE REACTIONS 237 Nucleophilic
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O BnO Ph Et 2N O BnO H 317 O O HO N
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NH 2 NH 2 Boc N H2N N(OH)Bn Boc N P
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NITRONE REACTIONS 243 EtAlCl2, TiCl
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NITRONE REACTIONS 245 Addition of v
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HO R R R HO N Bn NHBoc NH 2 NHBoc N
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RCHO BocNHOH R 2 + + O N R1 − PhS
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BzlOOC + NH3 Cl i OH BzlO Cl Cl Bzl
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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
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353 b a BnO BnO 354 Bn N CHO OBn b
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Table 2.13 Addition of organolithiu
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R N O Cl 367 −O + N Bu t LDA, THF
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HO HO OH N N • Ph • O OH O HO P
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RO2C N O X • N O • N O N O •
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N O 373 N O a 374, 376, 377 R2 376
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+ N O − HN HO O R1 S R2 R3 + Ph 1
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+ R 1 N R2 O O R 1 N R 2 − R 1 R
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NITRONE REACTIONS 273 Table 2.14 Sy
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+ Ph N O − Bn + O Et 3SiO MeO O H
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O O O N Pri OCOPh R Me Bn CO 2H NHC
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N O OBu t N O THF,−78°C, 1 h OBu
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O O O O 292 O H N −O + Bn O HO N
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NITRONE REACTIONS 283 The reaction
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O − O O BnO O O + O − O − N P
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R 1 R 2 NH 2 COOH Br a: b: c: d: e:
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NITRONE REACTIONS 289 2.6.6.1.11. N
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NITRONE REACTIONS 291 Nucleophilic
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O − O O + NBoc− O NBoc N Bn 1.
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NITRONE APPLICATION IN RADICAL POLY
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REACTIONS OF DIPOLAR 1,3-CYCLOADDIT
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a b c d REACTIONS OF DIPOLAR 1,3-CY
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R REACTIONS OF DIPOLAR 1,3-CYCLOADD
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a REACTIONS OF DIPOLAR 1,3-CYCLOADD
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− REACTIONS OF DIPOLAR 1,3-CYCLOA
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(a) REACTIONS OF DIPOLAR 1,3-CYCLOA
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O HO REACTIONS OF DIPOLAR 1,3-CYCLO
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Page 352 and 353:
Bn REACTIONS OF DIPOLAR 1,3-CYCLOAD
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CO 2Me O O REACTIONS OF DIPOLAR 1,3
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H H REACTIONS OF DIPOLAR 1,3-CYCLOA
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Me REACTIONS OF DIPOLAR 1,3-CYCLOAD
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O REACTIONS OF DIPOLAR 1,3-CYCLOADD
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Ph Ph REACTIONS OF DIPOLAR 1,3-CYCL
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− O Me REACTIONS OF DIPOLAR 1,3-C
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Ph REACTIONS OF DIPOLAR 1,3-CYCLOAD
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B C A Closed [5,6] adduct B B KINUG
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KINUGASA REACTION ([2 + 2] CYCLOADD
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O O N N N O R R O O L 1 : N N N 1 m
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R 1 R 1 O + N 774 a-e Δ O N N Ph 1
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783 784 + N O + CH3 − N O Ph CH3
Page 410 and 411:
R 1 NHOH 793 + R 2 CHO 794 Hydroxyl
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REACTIONS WITH CYCLOPROPANES 397 O
Page 414 and 415:
REFERENCES 399 properties and synth
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REFERENCES 401 (d) Mottley C, Mason
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REFERENCES 403 46. Sankuratri N, Ja
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REFERENCES 405 105. Saladino R, Ner
Page 422 and 423:
REFERENCES 407 159. Sridharan V, Mu
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REFERENCES 409 205. Cupone G, De Ni
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REFERENCES 411 259. Balasundaram B,
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REFERENCES 413 310. (a) Cicchi S, M
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REFERENCES 415 (b) Creary X. Acc. C
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REFERENCES 417 410. Dziembowska T,
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REFERENCES 419 459. Bourquet E, Ban
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REFERENCES 421 Papers of 6-th Inter
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REFERENCES 423 573. Ok D, Fisher MH
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REFERENCES 425 636. (a) Jost S, Gim
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REFERENCES 427 690. Haire DL, Janze
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REFERENCES 429 721. Manzoni L, Aros
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REFERENCES 431 762. Baldwin JE, Adl
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REFERENCES 433 808. Leggio A, Liguo
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3 Nitronates SEMA L. IOFFE N. D. Ze
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SYNTHESIS OF NITRONATES 437 as O-nu
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SYNTHESIS OF NITRONATES 439 These r
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SYNTHESIS OF NITRONATES 441 It shou
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X-C(NO 2) 3 NO 2-C(NO 2) 3 R R′ C
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R R′ X NO 2 base −H + R R′ X
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Br NaNO 2/DMF Cl R 6 R=C6H5; CO2MeR
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OH NO 2 R EtO2CN NCO 2Et PPh 3, ben
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NO 2 O Me R 2 R 1 PhSH Et 3N cat. M
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R R O OAc 19 Mn III −H + NO2 Me M
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Ag[ArC(NO2)2] 26 heptane 100°, 50
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NO2CH=C(NO2)Ph [RR′CN 2 28 RR′C
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Me O 2N Me O 2N 29a Br EtO 2CC CCO
Page 476 and 477:
SYNTHESIS OF NITRONATES 461 (39) (s
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SYNTHESIS OF NITRONATES 463 In the
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R 1 R R 2 NO 2 + R 5 R 3 42 43 R 6
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O O N R + R"CO NO2 R′ N 42 43c Ph
Page 484 and 485:
SYNTHESIS OF NITRONATES 469 3.2.2.3
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R R′ C R H C R′ NO2 [RR′C(NO2
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Table 3.1 The silylation of AN by E
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SYNTHESIS OF NITRONATES 475 Table 3
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O Me 2RSi NMe 2 + − Me2N=C—OSiM
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SYNTHESIS OF NITRONATES 479 decompo
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A G N R O N H O O A Si R 1 RR 1 C=N
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NO2CH2CH2CH2CO2ME Me CO2Me NO2CH CH
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SYNTHESIS OF NITRONATES 485 than 20
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R 1 R 2 LDA THF, −78°C R 1 O OLi
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O R 1 N 51o-t OSiMe2R 3 R 2 PRINCIP
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MeO2C H PRINCIPAL PHYSICOCHEMICAL D
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PRINCIPAL PHYSICOCHEMICAL DATA AND
Page 510 and 511:
R' R PRINCIPAL PHYSICOCHEMICAL DATA
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Table 3.8 (continued) PRINCIPAL PHY
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Page 522 and 523:
Page 524 and 525:
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Page 528 and 529:
** NO2 O O N O * N SiMe3 O PRINCIPA
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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 −
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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
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R 3 R 1 O R 4 R 3 R 3 R 1 R 1 55%-7
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RR′C N MeOCO MeO C O OBEt 2 N O O
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REACTIVITY OF NITRONATES 533 Yields
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RO R 4 R 3 R 2 O N R 1 O P(OAlk) 3
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REACTIVITY OF NITRONATES 537 Second
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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
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R R O2N O2N O N Regioselectivity +
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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.
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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
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RCH2NO2 RHC N RHC N O OH Ac 2O/AcON
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PhCOCH2SCHR′R′′ 180 R′R′
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REACTIVITY OF NITRONATES 561 Both o
Page 578 and 579:
R 185 + R′ 195 NO2 OH ( )n KH; TH
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NaNO2 AcOH 199 200 (+) -citronellen
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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′
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R′ R′ R′ R′ O N OSi 229 OH
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R′′ OH Si - Me2Bu t Si R′ R N
Page 592 and 593:
R = Me R′ = Ph(86%);CO2Me(28%) O
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R′O HO OR′ R′′ R′ O N * *
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REACTIVITY OF NITRONATES 581 orient
Page 598 and 599:
REACTIVITY OF NITRONATES 583 isomer
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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 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 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 648 and 649: R O N OX SILYLATION OF NITRO COMPOU
Page 654 and 655: (a) SiO O N 6 Nu (b) N N (c) SiO Si
Page 662 and 663: # N CO2Me OSi OMe SiO N CO2Me OSi S
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 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 694 and 695: R 2 SILYLATION OF NITRO COMPOUNDS 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 702 and 703:
SILYLATION OF NITRO COMPOUNDS AS A
Page 704 and 705:
RN(NO2)SiMe3 RN N + 473a,b OSiMe3 i
Page 706 and 707:
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 714 and 715:
Page 716 and 717:
Me Me Me Me Me Me Ph eq O 507a Ph N
Page 718 and 719:
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 728 and 729:
Page 730 and 731:
Page 732 and 733:
Page 734 and 735:
Page 736 and 737:
Me 3SiO Me3SiO N Me3SiON Me 3Si H N
Page 738 and 739:
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 746 and 747:
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:
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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