Foreword |
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Preface |
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vii | |
About the Authors |
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ix | |
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1 | (20) |
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1 | (1) |
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Occurrence and production |
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2 | (3) |
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Physical properties of bismuth |
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5 | (3) |
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Chemical properties of bismuth |
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8 | (1) |
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Bismuth compounds commercially available |
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9 | (4) |
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Present-day use of bismuth |
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13 | (5) |
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13 | (2) |
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Use in electronics, ceramics and plastics |
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15 | (1) |
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Use in chemicals and pigments |
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16 | (1) |
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Pharmaceutical and cosmetic use |
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17 | (1) |
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Toxicology of bismuth and bismuth compounds |
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18 | (3) |
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Organobismuth(III) Compounds |
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21 | (226) |
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Organobismuth(III) compounds with Bi--Group 14 element bonds |
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21 | (52) |
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Monoorganyl and diorganylbismuthines |
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21 | (1) |
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22 | (1) |
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22 | (1) |
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22 | (5) |
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27 | (1) |
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28 | (1) |
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29 | (1) |
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29 | (1) |
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Via reduction of triarylbismuth dihalides |
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30 | (1) |
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Via thermolysis of bismuth sulfinates |
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30 | (1) |
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Via electrochemical alkylation |
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31 | (1) |
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From organic halides and bismuth metal |
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31 | (1) |
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31 | (1) |
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32 | (1) |
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33 | (1) |
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Transformation of the substituted groups |
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33 | (1) |
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Disproportionation of mixed triorganylbismuthine |
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34 | (24) |
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58 | (4) |
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62 | (11) |
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Organobismuth(III) compounds with Bi--Group 15 or Bi--Group 16 element bonds |
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73 | (125) |
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Diorganylbismuth compounds |
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73 | (1) |
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73 | (3) |
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76 | (1) |
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Diorganylbismuth compounds with Bi--N bonds |
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76 | (3) |
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Diorganylbismuth compounds with Bi--As or Bi--Sb bonds |
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79 | (3) |
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Diorganylbismuth compounds with Bi--O bonds |
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82 | (9) |
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Diorganylbismuth compounds with Bi--S bonds |
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91 | (7) |
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Diorganylbismuth compounds with Bi--Se or Bi--Te bonds |
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98 | (5) |
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Cationic and anionic diorganylbismuth compounds |
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103 | (4) |
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Dibismuthines and dibismuthene |
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107 | (1) |
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Methods of synthesis of dibismuthines |
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107 | (8) |
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Physical properties of dibismuthines |
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115 | (1) |
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Chemical properties of dibismuthines |
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116 | (3) |
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119 | (2) |
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Monoorganylbismuth compounds |
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121 | (1) |
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121 | (3) |
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124 | (1) |
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Monoorganylbismuth compounds with Bi--N bonds |
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124 | (1) |
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Monoorganylbismuth compounds with Bi--O bonds |
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125 | (7) |
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Monoorganylbismuth compounds with Bi--S bonds |
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132 | (9) |
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Monoorganylbismuth compounds with Bi--Se or Bi--Te bonds |
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141 | (1) |
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Cationic and anionic monoorganylbismuth compounds |
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142 | (3) |
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Bismuth(III) compounds with three Bi--Group 15 or 16 element bonds |
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145 | (1) |
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145 | (3) |
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Bismuth(III) compounds with three Bi--N bonds |
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148 | (6) |
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Bismuth(III) compounds with three Bi--O bonds |
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154 | (12) |
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Bismuth(III) compounds with three Bi--S bonds |
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166 | (29) |
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Bismuth(III) compounds with three Bi--Se bonds |
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195 | (3) |
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Organobismuth(III) compounds with Bi--Group 17 element bonds |
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198 | (34) |
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198 | (1) |
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198 | (1) |
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198 | (1) |
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199 | (1) |
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200 | (1) |
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201 | (2) |
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From alkyl halides and bismuth metal |
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203 | (1) |
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From germylbismuthines and hydrogen chloride |
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204 | (1) |
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204 | (1) |
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204 | (1) |
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From diazonium salt--bismuth halide complexes |
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205 | (1) |
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Transformation of the substituted group |
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205 | (1) |
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Halobismuthine complex salts and related compounds |
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205 | (1) |
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Arene--bismuth halide π-complexes |
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206 | (17) |
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223 | (6) |
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229 | (3) |
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Triorganylbismuthine--transition metal complexes |
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232 | (7) |
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232 | (1) |
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233 | (6) |
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Organobismuth(III) compounds with Bi--transition metal linkage |
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239 | (8) |
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239 | (1) |
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240 | (7) |
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Organobismuth(V) Compounds |
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247 | (82) |
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Triorganylbismuth dihalides and related compounds |
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247 | (32) |
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247 | (1) |
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Oxidative addition to triorganylbismuthines |
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247 | (2) |
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Via metathetical reaction of triarylbismuth dihalides and related compounds |
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249 | (2) |
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Via miscellaneous approaches |
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251 | (21) |
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272 | (2) |
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274 | (5) |
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Oxybis(triorganylbismuth) compounds |
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279 | (6) |
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279 | (1) |
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From triarylbismuth dihalides |
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279 | (1) |
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From other oxybis(triarylbismuth) compounds |
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280 | (1) |
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Ligand coordination to oxybis(triarylbismuth) compounds |
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281 | (2) |
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283 | (2) |
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Quaternary organobismuth(V) compounds |
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285 | (16) |
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285 | (1) |
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From quinquenary organobismuth compounds |
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285 | (1) |
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From quaternary organobismuth compounds |
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285 | (1) |
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Via disproportionation of triarylbismuth dihalides |
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286 | (1) |
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From triarylbismuth difluorides and organometallic reagents |
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287 | (1) |
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From tertiary bismuthines |
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288 | (8) |
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296 | (2) |
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298 | (3) |
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Quinquenary organobismuth(V) and related compounds |
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301 | (5) |
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301 | (1) |
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From triorganylbismuth dihalides |
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301 | (1) |
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From triphenylbismuthimine imides |
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301 | (1) |
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301 | (3) |
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304 | (2) |
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306 | (7) |
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306 | (1) |
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From triphenylbismuthine and diazo compounds |
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306 | (1) |
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From triarylbismuth(V) compounds |
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306 | (1) |
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From bismuthonium salts and base |
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307 | (2) |
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309 | (1) |
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310 | (3) |
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313 | (6) |
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313 | (1) |
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From tertiary bismuthines |
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313 | (1) |
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From triarylbismuth dihalides and sulfonamides or amides |
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313 | (3) |
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316 | (3) |
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Bismuthinates and bismuthinic acids |
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319 | (3) |
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319 | (1) |
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320 | (2) |
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Triorganylbismuthine oxides |
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322 | (7) |
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322 | (1) |
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Metathesis of triorganylbismuth(V) compounds |
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322 | (1) |
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Direct oxidation of tertiary bismuthines |
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323 | (2) |
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325 | (1) |
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326 | (3) |
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Bismuth-Containing Heterocycles |
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329 | (42) |
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329 | (16) |
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329 | (6) |
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335 | (3) |
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338 | (1) |
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Bicyclic compounds with bridgehead bismuth atom or atoms |
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339 | (6) |
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345 | (26) |
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Oxabismoles and derivatives |
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345 | (5) |
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Oxabismabenzene and related compounds |
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350 | (1) |
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351 | (1) |
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Miscellaneous bismuth-containing heterocycles |
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352 | (1) |
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Heterobismacycles containing a chalcogen--bismuth--chalcogen bond in the ring system |
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352 | (2) |
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Heterobismacycles with no carbon atom ring |
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354 | (17) |
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Bismuth Compounds in Organic Transformations |
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371 | (70) |
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371 | (1) |
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372 | (25) |
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372 | (1) |
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372 | (8) |
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380 | (1) |
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Bismuth oxide and mixed bismuth/metal oxide systems as oxidant or oxidation catalyst |
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380 | (1) |
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Oxidation with bismuth oxide |
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380 | (2) |
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Oxidation of olefins over bismuth molybdate-based catalysts |
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382 | (2) |
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Miscellaneous oxidations using other mixed bismuth/metal oxide-based catalysts |
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384 | (3) |
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387 | (5) |
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Organobismuth(V) compounds |
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392 | (5) |
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397 | (4) |
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Carbon--carbon bond forming reactions |
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401 | (24) |
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Bi(0)-promoted carbon--carbon bond forming reactions |
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401 | (2) |
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Bismuth(III) salt-catalyzed carbon--carbon bond forming reactions |
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403 | (7) |
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Carbon-carbon bond forming reactions using organobismuth compounds |
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410 | (1) |
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410 | (7) |
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Transition metal-catalyzed carbon--carbon bond forming reactions |
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417 | (2) |
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Carbon--carbon bond forming reactions based on bismuthonium salts and ylides |
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419 | (4) |
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Miscellaneous carbon--carbon bond forming reactions |
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423 | (2) |
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Carbon--heteroatom bond forming reactions |
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425 | (16) |
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Reactions with bismuth(III) salt |
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425 | (1) |
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Carbon--oxygen bond forming reactions |
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425 | (2) |
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Carbon--sulfur bond forming reactions |
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427 | (1) |
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Carbon--nitrogen bond forming reactions |
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428 | (1) |
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Carbon--halogen bond forming reactions |
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429 | (2) |
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Reactions with organobismuth compounds |
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431 | (1) |
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431 | (4) |
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N-Arylation and S-arylation |
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435 | (3) |
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Miscellaneous carbon-heteroatom bond forming reactions |
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438 | (3) |
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Structural Chemistry of Organobismuth Compounds |
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441 | (106) |
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Fundamental structure parameters |
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441 | (1) |
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441 | (1) |
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442 | (1) |
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Structures of organobismuth compounds |
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442 | (105) |
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442 | (4) |
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446 | (1) |
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447 | (2) |
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449 | (2) |
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451 | (1) |
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452 | (1) |
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453 | (1) |
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Polymeric structure of organobismuth compounds |
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454 | (1) |
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455 | (1) |
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456 | (1) |
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456 | (91) |
Formula Index for X-Ray Data |
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547 | (8) |
Abbreviations and Symbols |
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555 | (4) |
Procedure Index |
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559 | (6) |
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Preparation of selected organobismuth compounds |
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559 | (3) |
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Organic transformations based on bismuth compounds |
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562 | (3) |
Reference Code Index |
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565 | (6) |
References |
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571 | |
Subject Index |
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61 | |