Weygand/Hilgetag Preparative Organic Chemistry

More documents

Recommendations

Info

842 Formation of carbon-carbon multiple bonds dizing vicinal dihydrazones with silver trifluoroacetate and triethylamine with acetonitrile or ethanol as solvent: 208 C6H5 C—CC6H5 || || + 4CF3COOAg+ 4N(C2H5)3 > NH2—N N—NH2 C6H5C=CC6H5 + 4(C2H5)3NH + [CF3COO]- + 4Ag + 2N2 Certain cyclic acetylenic compounds can also be synthesized by this method, e.g., cyclodecyne 209 in 36% yield by oxidation of 1,2-cyclodecanedione dihydrazone with yellow mercuric oxide in benzene containing ethanolic potassium hydroxide solution and anhydrous sodium sulfate; and cyclodecyne has been obtained similarly. 210 [CH2], | z HgO in benzene Several reviews 211 are available for consultation regarding the preparation of acetylenes. 208 M. S. Nemwan and D. E. Reid, /. Org. Chem., 23, 665 (1958). 209 A. T. Blomquist, R. E. Burge, and A. C. Sucsy, /. Amer. Chem. Soc, 74, 3636 (1952). 210 V. Prelog and M. Speck, Helv. Chim. Acta, 38, 1790 (1952). 211 T. L. Jacobs, Org. Reactions, 5, 1 (1949); W. Franke, W. Ziegenbein, and H. Meister, Angew. Chem., 72, 392 (1960); J. F. Arens, Advan. Org. Chem., 2, 121 (1960).
PARTB Formation of new carbon-carbon bonds
Page 1 and 2:
PREPARATIVE ORGANIC CHEMISTRY
Page 3 and 4:
WEYGAND/HILGETAG PREPARATIVE ORGANI
Page 5 and 6:
Foreword to the 4 th Edition The fi
Page 7:
Summary of Contents Introduction: O
Page 10 and 11:
X Contents II. Addition of hydrogen
Page 12 and 13:
x ii Contents II. Replacement of ha
Page 14 and 15:
xiv Contents II. Esters 368 1. Repl
Page 16 and 17:
xvi Contents 1. Replacement of nitr
Page 18 and 19:
xviii Contents 5. Cleavage of the S
Page 20 and 21:
xx Contents Chapter 11. Formation o
Page 22 and 23:
xxii Contents 1.3. Formation of new
Page 24 and 25:
xxiv Contents IV. Rearrangement of
Page 27 and 28:
Introduction: Organization of the M
Page 29:
PART A Reactions on the Intact Carb
Page 32 and 33:
6 Formation of carbon-hydrogen bond
Page 34 and 35:
8 Formation of carbon-hydrogen bond
Page 36 and 37:
10 Formation of carbon-hydrogen bon
Page 38 and 39:
Page 40 and 41:
Page 42 and 43:
Page 44 and 45:
Page 46 and 47:
Page 48 and 49:
Page 50 and 51:
Page 52 and 53:
Page 54 and 55:
Page 56 and 57:
Page 58 and 59:
Page 60 and 61:
Page 62 and 63:
Page 64 and 65:
Page 66 and 67:
Page 68 and 69:
Page 70 and 71:
Page 72 and 73:
Page 74 and 75:
Page 76 and 77:
Page 78 and 79:
Page 80 and 81:
Page 82 and 83:
Page 84 and 85:
Page 86 and 87:
Page 88 and 89:
Page 90 and 91:
Page 92 and 93:
Page 94 and 95:
Page 96 and 97:
Page 98 and 99:
Page 100 and 101:
Page 102 and 103:
Page 104 and 105:
Page 106 and 107:
Page 108 and 109:
Page 110 and 111:
Page 112 and 113:
86 Formation of carbon-deuterium bo
Page 114 and 115:
Page 116 and 117:
Page 118 and 119:
Page 120 and 121:
Page 122 and 123:
Page 124 and 125:
Page 126 and 127:
100 Formation of carbon-deuterium b
Page 128 and 129:
CHAPTER 3 Formation of Carbon-Halog
Page 130 and 131:
104 Formation of carbon-halogen bon
Page 132 and 133:
Page 134 and 135:
Page 136 and 137:
Page 138 and 139:
Page 140 and 141:
Page 142 and 143:
Page 144 and 145:
Page 146 and 147:
Page 148 and 149:
Page 150 and 151:
Page 152 and 153:
Page 154 and 155:
Page 156 and 157:
Page 158 and 159:
Page 160 and 161:
Page 162 and 163:
Page 164 and 165:
Page 166 and 167:
Page 168 and 169:
Page 170 and 171:
Page 172 and 173:
Page 174 and 175:
Page 176 and 177:
Page 178 and 179:
Page 180 and 181:
Page 182 and 183:
Page 184 and 185:
Page 186 and 187:
Page 188 and 189:
Page 190 and 191:
Page 192 and 193:
Page 194 and 195:
Page 196 and 197:
Page 198 and 199:
Page 200 and 201:
Page 202 and 203:
Page 204 and 205:
Page 206 and 207:
Page 208 and 209:
Page 210 and 211:
Page 212 and 213:
Page 214 and 215:
Page 216 and 217:
Page 218 and 219:
Page 220 and 221:
Page 222 and 223:
Page 224 and 225:
Page 226 and 227:
Page 228 and 229:
Page 230 and 231:
Page 232 and 233:
Page 234 and 235:
Page 236 and 237:
Page 238 and 239:
Page 240 and 241:
Page 242 and 243:
Page 244 and 245:
Page 246 and 247:
Page 248 and 249:
Page 250 and 251:
Page 252 and 253:
Page 254 and 255:
Page 256 and 257:
Page 258 and 259:
Page 260 and 261:
Page 262 and 263:
Page 264 and 265:
Page 266 and 267:
240 Formation of c arbon-halogen bo
Page 268 and 269:
Page 270 and 271:
Page 272 and 273:
Page 274 and 275:
Page 276 and 277:
Page 278 and 279:
Page 280 and 281:
Page 282 and 283:
Page 284 and 285:
Page 286 and 287:
Page 288 and 289:
Page 290 and 291:
Page 292 and 293:
Page 294 and 295:
Page 296 and 297:
Page 298 and 299:
Page 300 and 301:
274 Formation of carbon-oxygen bond
Page 302 and 303:
Page 304 and 305:
Page 306 and 307:
Page 308 and 309:
Page 310 and 311:
Page 312 and 313:
Page 314 and 315:
Page 316 and 317:
Page 318 and 319:
Page 320 and 321:
Page 322 and 323:
Page 324 and 325:
Page 326 and 327:
Page 328 and 329:
Page 330 and 331:
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:
Page 348 and 349:
Page 350 and 351:
Page 352 and 353:
Page 354 and 355:
Page 356 and 357:
Page 358 and 359:
Page 360 and 361:
Page 362 and 363:
Page 364 and 365:
Page 366 and 367:
Page 368 and 369:
Page 370 and 371:
Page 372 and 373:
Page 374 and 375:
Page 376 and 377:
Page 378 and 379:
Page 380 and 381:
Page 382 and 383:
Page 384 and 385:
Page 386 and 387:
Page 388 and 389:
Page 390 and 391:
Page 392 and 393:
Page 394 and 395:
Page 396 and 397:
Page 398 and 399:
Page 400 and 401:
Page 402 and 403:
Page 404 and 405:
Page 406 and 407:
Page 408 and 409:
Page 410 and 411:
Page 412 and 413:
Page 414 and 415:
Page 416 and 417:
Page 418 and 419:
392 Cleavage of carbon-oxygen bonds
Page 420 and 421:
Page 422 and 423:
Page 424 and 425:
Page 426 and 427:
Page 428 and 429:
Page 430 and 431:
CHAPTER 6 Formation of Carbon-Nitro
Page 432 and 433:
406 Formation of carbon-nitrogen bo
Page 434 and 435:
Page 436 and 437:
Page 438 and 439:
Page 440 and 441:
Page 442 and 443:
Page 444 and 445:
Page 446 and 447:
Page 448 and 449:
Page 450 and 451:
Page 452 and 453:
Page 454 and 455:
Page 456 and 457:
Page 458 and 459:
Page 460 and 461:
Page 462 and 463:
Page 464 and 465:
Page 466 and 467:
Page 468 and 469:
Page 470 and 471:
Page 472 and 473:
Page 474 and 475:
Page 476 and 477:
Page 478 and 479:
Page 480 and 481:
Page 482 and 483:
Page 484 and 485:
Page 486 and 487:
Page 488 and 489:
Page 490 and 491:
Page 492 and 493:
Page 494 and 495:
Page 496 and 497:
Page 498 and 499:
Page 500 and 501:
Page 502 and 503:
Page 504 and 505:
Page 506 and 507:
Page 508 and 509:
Page 510 and 511:
Page 512 and 513:
Page 514 and 515:
48 8 Formation of carbon-nitrogen b
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:
Page 530 and 531:
Page 532 and 533:
Page 534 and 535:
Page 536 and 537:
Page 538 and 539:
Page 540 and 541:
Page 542 and 543:
Page 544 and 545:
Page 546 and 547:
Page 548 and 549:
Page 550 and 551:
Page 552 and 553:
Page 554 and 555:
Page 556 and 557:
Page 558 and 559:
Page 560 and 561:
Page 562 and 563:
Page 564 and 565:
Page 566 and 567:
Page 568 and 569:
Page 570 and 571:
Page 572 and 573:
Page 574 and 575:
Page 576 and 577:
550 Alteration of nitrogen groups i
Page 578 and 579:
Page 580 and 581:
Page 582 and 583:
Page 584 and 585:
Page 586 and 587:
Page 588 and 589:
Page 590 and 591:
Page 592 and 593:
Page 594 and 595:
Page 596 and 597:
Page 598 and 599:
Page 600 and 601:
Page 602 and 603:
Page 604 and 605:
Page 606 and 607:
Page 608 and 609:
Page 610 and 611:
Page 612 and 613:
Page 614 and 615:
Page 616 and 617:
Page 618 and 619:
Page 620 and 621:
Page 622 and 623:
Page 624 and 625:
Page 626 and 627:
CHAPTER 8 Formation of Carbon-Sulfu
Page 628 and 629:
602 Formation of carbon-sulfur bond
Page 630 and 631:
Page 632 and 633:
Page 634 and 635:
Page 636 and 637:
Page 638 and 639:
Page 640 and 641:
Page 642 and 643:
Page 644 and 645:
Page 646 and 647:
Page 648 and 649:
Page 650 and 651:
Page 652 and 653:
Page 654 and 655:
Page 656 and 657:
Page 658 and 659:
Page 660 and 661:
Page 662 and 663:
Page 664 and 665:
Page 666 and 667:
Page 668 and 669:
Page 670 and 671:
Page 672 and 673:
Page 674 and 675:
Page 676 and 677:
Page 678 and 679:
Page 680 and 681:
Page 682 and 683:
Page 684 and 685:
Page 686 and 687:
Page 688 and 689:
Page 690 and 691:
Page 692 and 693:
Page 694 and 695:
Page 696 and 697:
Page 698 and 699:
Page 700 and 701:
Page 702 and 703:
Page 704 and 705:
Page 706 and 707:
Page 708 and 709:
Page 710 and 711:
Page 712 and 713:
Page 714 and 715:
Page 716 and 717:
Page 718 and 719:
Page 720 and 721:
694 Formation of carbon-phosphorus
Page 722 and 723:
Page 724 and 725:
Page 726 and 727:
Page 728 and 729:
Page 730 and 731:
Page 732 and 733:
Page 734 and 735:
Page 736 and 737:
Page 738 and 739:
Page 740 and 741:
Page 742 and 743:
Page 744 and 745:
Page 746 and 747:
Page 748 and 749:
Page 750 and 751:
Page 752 and 753:
Page 754 and 755:
Page 756 and 757:
Page 758 and 759:
Page 760 and 761:
Page 762 and 763:
Page 764 and 765:
Page 766 and 767:
Page 768 and 769:
Page 770 and 771:
Page 772 and 773:
Page 774 and 775:
CHAPTER 10 Formation of Metal-Carbo
Page 776 and 777:
750 Formation of metal-carbon bonds
Page 778 and 779:
7 52 Formation of metal-carbon bond
Page 780 and 781:
Page 782 and 783:
Page 784 and 785:
Page 786 and 787:
Page 788 and 789:
Page 790 and 791:
Page 792 and 793:
Page 794 and 795:
Page 796 and 797:
Page 798 and 799:
Page 800 and 801:
Page 802 and 803:
Page 804 and 805:
Page 806 and 807:
Page 808 and 809:
Page 810 and 811:
Page 812 and 813:
Page 814 and 815:
Page 816 and 817:
Page 818 and 819: 792 Formation of metal-carbon bonds
Page 840 and 841: 814 Formation of carbon-carbon mult
Page 871 and 872: PARTB Formation of new carbon-carbo
Page 873 and 874: Addition to C=C bonds 847 Under the
Page 875 and 876: Addition to C= C bonds 849 A radica
Page 877 and 878: Addition to C=C bonds 851 ful catal
Page 879 and 880: formation (b) that is necessary for
Page 881 and 882: Addition to C —C bonds 855 Nitril
Page 883 and 884: Addition to C —C bonds 857 3,6-ep
Page 885 and 886: Addition to C—C bonds 8 59 Stereo
Page 887 and 888: Addition to C=C bonds 861 6. Additi
Page 889 and 890: Addition to C=C bonds 863 In this c
Page 891 and 892: Addition to C=C bonds 865 are added
Page 893 and 894: Addition to C=C bonds 867 amount of
Page 895 and 896: Addition to the C=O bond 869 Such a
Page 897 and 898: Addition to the C=O bond 871 Such c
Page 899 and 900: Addition to the C=O bond 873 3. For
Page 901 and 902: Addition to the C=O bond 875 In hyd
Page 903 and 904: Addition to the C=O bond 877 Finely
Page 905 and 906: Addition to the C=O bond 879 the te
Page 907 and 908: Addition to the C=O bond 881 A Grig
Page 909 and 910: Addition to the C=O bond 883 c. Tre
Page 911 and 912: Addition to the C= O bond 885 The d
Page 913 and 914: Addition to C-N multiple bonds 887
Page 919 and 920:
Addition to C-N multiple bonds 893
Page 921 and 922:
C-C linkage by removal of hydrogen
Page 923 and 924:
C~C linkage by removal of hydrogen
Page 925 and 926:
Page 927 and 928:
Page 929 and 930:
C-C linkage by replacement of halog
Page 931 and 932:
Page 933 and 934:
Page 935 and 936:
Page 937 and 938:
Page 939 and 940:
Page 941 and 942:
Page 943 and 944:
Page 945 and 946:
Page 947 and 948:
Page 949 and 950:
Page 951 and 952:
Page 953 and 954:
Page 955 and 956:
Page 957 and 958:
Page 959 and 960:
Page 961 and 962:
Page 963 and 964:
Page 965 and 966:
Page 967 and 968:
Page 969 and 970:
Page 971 and 972:
Page 973 and 974:
Page 975 and 976:
esters: 634 ' 640 ' 641 C-C linkage
Page 977 and 978:
C-C linkage by replacement of hydro
Page 979 and 980:
Page 981 and 982:
Page 983 and 984:
Page 985 and 986:
C-C linkage by replacement of OR by
Page 987 and 988:
Page 989 and 990:
Page 991 and 992:
C-C linkage by replacement of O-acy
Page 993 and 994:
C-C linkage by replacement of nitro
Page 995 and 996:
Page 997 and 998:
Page 999 and 1000:
tions (see also page 957): C-C link
Page 1001 and 1002:
Page 1003 and 1004:
Page 1005 and 1006:
Removal of halogen with formation o
Page 1007 and 1008:
Formation of a new C=C bond by remo
Page 1009 and 1010:
Page 1011 and 1012:
Page 1013 and 1014:
Page 1015 and 1016:
Page 1017 and 1018:
Page 1019 and 1020:
Page 1021 and 1022:
Removal of sulfur with formation of
Page 1023 and 1024:
Removal of phosphorus with formatio
Page 1025:
Removal of phosphorus with formatio
Page 1029 and 1030:
PART C Cleavage of Carbon-Carbon Bo
Page 1031 and 1032:
Removal of carbon dioxide 1005 Only
Page 1033 and 1034:
Removal of carbon dioxide 1007 resp
Page 1035 and 1036:
Removal of carbon dioxide 1009 e. N
Page 1037 and 1038:
Removal of carbon dioxide 1011 Hydr
Page 1039 and 1040:
Removal of carbon d ioxide 1013 Thi
Page 1041 and 1042:
Removal of carbon d ioxide 1015 as
Page 1043 and 1044:
Removal of carbon dioxide 1017 char
Page 1045 and 1046:
Removal of carbon dioxide 1019 Conv
Page 1047 and 1048:
Removal of carbon monoxide 1021 Thi
Page 1049 and 1050:
Removal of carbon monoxide 1023 lab
Page 1051 and 1052:
Removal of carbon monoxide 1025 It
Page 1053 and 1054:
Removal of other fragments 1027 1.
Page 1055 and 1056:
Removal of other fragments 1029 sol
Page 1057 and 1058:
Removal of other fragments 1031 The
Page 1059 and 1060:
Oxidative cleavage of C-C bonds in
Page 1061 and 1062:
Oxidative degradation of olefins 10
Page 1063 and 1064:
Page 1065 and 1066:
Page 1067 and 1068:
Oxidative cleavage of carbon-carbon
Page 1069 and 1070:
Oxidative cleavage of carbon-carbon
Page 1071 and 1072:
Oxidative degradation of aromatic a
Page 1073 and 1074:
Hydrolytic cleavage 1047 Cleavage b
Page 1075:
Hydrolytic cleavage 1049 Ethyl acet
Page 1079 and 1080:
PART D Rearrangements of Carbon Com
Page 1081 and 1082:
Migration of a multiple bond 1055 i
Page 1083 and 1084:
Migration of a multiple bond 1057 A
Page 1085 and 1086:
Rearrangement with change of an oxy
Page 1087 and 1088:
Page 1089 and 1090:
Page 1091 and 1092:
2 hours at 250-270°, thus: 54 Rear
Page 1093 and 1094:
Rearrangement of halogen compounds
Page 1095 and 1096:
Migration from oxygen to carbon 106
Page 1097 and 1098:
Migration from oxygen to carbon 107
Page 1099 and 1100:
Migration from nitrogen to carbon 1
Page 1101 and 1102:
Benzyl-0-tolyl rearrangement 1075 R
Page 1103 and 1104:
Migration from carbon to nitrogen 1
Page 1105 and 1106:
Page 1107 and 1108:
Page 1109 and 1110:
Wagner-Meerwein rearrangement and r
Page 1111 and 1112:
Wagner-Meerwein rearrangement and r
Page 1113 and 1114:
Cope rearrangement; valence isomeri
Page 1115 and 1116:
Cope rearrangement; valence isomeri
Page 1117 and 1118:
Rearrangement on decomposition of d
Page 1119 and 1120:
Rearrangement on decomposition of d
Page 1121 and 1122:
Appendix I Purification and drying
Page 1123 and 1124:
Purification and drying of organic
Page 1125 and 1126:
Page 1127 and 1128:
Page 1129 and 1130:
Preparation and purification of gas
Page 1131 and 1132:
Preparation and purification of gas
Page 1133 and 1134:
Preparative organic work with small
Page 1135 and 1136:
Page 1137 and 1138:
Page 1139 and 1140:
Page 1141 and 1142:
Page 1143 and 1144:
Page 1145 and 1146:
Page 1147 and 1148:
Page 1149 and 1150:
Page 1151 and 1152:
Page 1153 and 1154:
Page 1155 and 1156:
SUBJECT INDEX This index deals prim
Page 1157 and 1158:
Acetophenone, co-amino-, 451 —, b
Page 1159 and 1160:
Aldehyde nitrates, 423 Aldehydes, a
Page 1161 and 1162:
Amidic acids, 485 Amidines, 472 —
Page 1163 and 1164:
Aporphine, 970 D-Arabinose, 1029
Page 1165 and 1166:
Benzene, pentaphenyl-, 831 — ,pen
Page 1167 and 1168:
Benzoyl chloride, 246 — —, 0-ch
Page 1169 and 1170:
Butane, l-bromo-4-chloro-, 238 —,
Page 1171 and 1172:
Carbodiimide, dicyclohexyl-, oxidat
Page 1173 and 1174:
Chloromethylation, 158, 952 (Chloro
Page 1175 and 1176:
Cyclohexanone, 2,3-epoxy-3,5,5-trim
Page 1177 and 1178:
Diethyl ether, sulfide, 637, 653
Page 1179 and 1180:
Ethane, 1,2-dichloro-, 107 —, 1 ,
Page 1181 and 1182:
Formic acid, esters, decomposition,
Page 1183 and 1184:
Heptatrienal, 7-phenyl-, 988 3-Hept
Page 1185 and 1186:
Hydroquinones, 0-mercapto, 606 Hydr
Page 1187 and 1188:
Ketones, (x,oc-dibromo, 191, 258
Page 1189 and 1190:
Methane, diphenyltolyl-, 949 —, n
Page 1191 and 1192:
l-Naphthylamines, JV-aryl-, 531, 53
Page 1193 and 1194:
Oxazole, 5-ethoxy-2-phenyl-, 858 Ox
Page 1195 and 1196:
Phenyl azide, 584 — isocyanate, 4
Page 1197 and 1198:
Propane, l,2,3-trichloro-2-methyl-,
Page 1199 and 1200:
2,6-Pyridinediamine, 443 3,5-Pyridi
Page 1201 and 1202:
Silane, trichloro(chloromethyl)-, 7
Page 1203 and 1204:
Sulfoxides, 630, 667, 668 —, redu
Page 1205 and 1206:
Thiouronium salts, 692 , S-cyclohex
Page 1207:
Valence isomerization, 1088 Valeral
show all

Weygand/Hilgetag Preparative Organic Chemistry

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?