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

More documents

Recommendations

Info

NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS Novel Strategies in Synthesis Second Edition Edited by Henry Feuer A JOHN WILEY & SONS, INC., PUBLICATION
Page 4: NITRILE OXIDES, NITRONES, AND NITRO
Page 7 and 8: Copyright © 2008 by John Wiley & S
Page 10: SERIES FOREWORD The beginning of al
Page 13 and 14: x LIST OF ABBREVIATIONS HMPA hexame
Page 16 and 17: 1 Nitrile Oxides LEONID I. BELEN’
Page 18 and 19: METHODS FOR GENERATION AND PREPARAT
Page 26 and 27: O − O − N + H N + H METHODS FOR
Page 28 and 29: N O NO S O2 16 17 R REACTIONS OF NI
Page 30 and 31: RCNO + NO 2 R NO2 C R C NO REACTION
Page 32 and 33: HetH: HetH + R-CCl=NOH N H N′ RCN
Page 34 and 35: REACTIONS OF NITRILE OXIDES 19 comp
Page 36 and 37: REACTIONS OF NITRILE OXIDES 21 4-ch
Page 38 and 39: O N O O 34 (R = CN, Ph, p-Tol, CH2B
Page 40 and 41: REACTIONS OF NITRILE OXIDES 25 viny
Page 42 and 43: Ph N O 48 REACTIONS OF NITRILE OXID
Page 44 and 45: H 2C C CH N R 2 R 1 54 ArCNO Ar Ar
Page 46 and 47: R CR 1 R 2 Me N R O 1 R2 R REACTION
Page 48 and 49: REACTIONS OF NITRILE OXIDES 33 It w
Page 50 and 51: R N O H H Fe(CO) 3 R N O R R N REAC
Page 52 and 53:
REACTIONS OF NITRILE OXIDES 37 thes
Page 54 and 55:
REACTIONS OF NITRILE OXIDES 39 oxat
Page 56 and 57:
H O N H N CN Bz R 2 R 1 R REACTIONS
Page 58 and 59:
REACTIONS OF NITRILE OXIDES 43 5,5-
Page 60 and 61:
O Ph S 124 NMe NO2 O Ph S Et3N ArNC
Page 62 and 63:
R R 1 132 CO 2R 2 N Ph Ph R 3 CNO R
Page 64 and 65:
N Ar COAr′ H MeOH N O Ar HN R NH
Page 66 and 67:
REACTIONS OF NITRILE OXIDES 51 gave
Page 68 and 69:
Me N O N Mes R N Me 162 REACTIONS O
Page 70 and 71:
REACTIONS OF NITRILE OXIDES 55 addu
Page 72 and 73:
t-Bu t-Bu PhC( NOH) 180 REACTIONS O
Page 74 and 75:
P R P R P R ArCNO −78 °C −r. t
Page 76 and 77:
REACTIONS OF NITRILE OXIDES 61 The
Page 78 and 79:
REACTIONS OF NITRILE OXIDES 63 seve
Page 80 and 81:
R 1 Ph O N R 217 218 REACTIONS OF N
Page 82 and 83:
REACTIONS OF NITRILE OXIDES 67 Diff
Page 84 and 85:
REACTIONS OF NITRILE OXIDES 69 A ph
Page 86 and 87:
REACTIONS OF NITRILE OXIDES 71 (R 6
Page 88 and 89:
REACTIONS OF NITRILE OXIDES 73 INOC
Page 90 and 91:
RCHO + + NH2 n = 1, 2 R′ H N O R
Page 92 and 93:
ArCNO + 359 CH2Cl OMe Ar ArCNO, BF3
Page 94 and 95:
RCNO NMO − NMM R = Ph, 4-ClC6H4,
Page 96 and 97:
REACTIONS OF NITRILE OXIDES 81 Benz
Page 98 and 99:
APPLICATIONS OF NITRILE OXIDES 83
Page 100 and 101:
O N N O Ph R O N N Me Me 395 R = Me
Page 102 and 103:
APPLICATIONS OF NITRILE OXIDES 87 I
Page 104 and 105:
Si O Si H Si O Si O N + ClC CCl NOH
Page 106 and 107:
APPLICATIONS OF NITRILE OXIDES 91 T
Page 108 and 109:
H H OMe 425 H CNO H CH2=CHCH2Br Sch
Page 110 and 111:
H2NC NH OH N O 432 APPLICATIONS OF
Page 112 and 113:
APPLICATIONS OF NITRILE OXIDES 97 T
Page 114 and 115:
O TBDPSO Me Me H APPLICATIONS OF NI
Page 116 and 117:
Me O O N O Me Me O APPLICATIONS OF
Page 118 and 119:
Page 120 and 121:
Page 122 and 123:
Page 124 and 125:
REFERENCES 109 5. Jager F, Colinas
Page 126 and 127:
REFERENCES 111 59. Das B, Holla H,
Page 128 and 129:
REFERENCES 113 116. Vovk MV, Romane
Page 130 and 131:
REFERENCES 115 179. Nicolaides DN,
Page 132 and 133:
REFERENCES 117 238. Adembri G, Gior
Page 134 and 135:
REFERENCES 119 294. Segi M. Yuki Go
Page 136 and 137:
REFERENCES 121 352. Chung W-Sh, Tsa
Page 138 and 139:
REFERENCES 123 412. Yeh M-ChP, Jou
Page 140 and 141:
REFERENCES 125 476. Fleming KN, Tay
Page 142:
REFERENCES 127 525. Lysenko Z, Wess
Page 145 and 146:
130 NITRONES: NOVEL STRATEGIES IN S
Page 147 and 148:
Page 149 and 150:
Page 151 and 152:
Page 153 and 154:
Page 155 and 156:
Page 157 and 158:
Page 159 and 160:
Page 161 and 162:
Page 163 and 164:
Page 165 and 166:
Page 167 and 168:
Page 169 and 170:
Page 171 and 172:
Page 173 and 174:
Page 175 and 176:
Page 177 and 178:
Page 179 and 180:
Page 181 and 182:
Page 183 and 184:
Page 185 and 186:
Page 187 and 188:
Page 189 and 190:
Page 191 and 192:
Page 193 and 194:
Page 195 and 196:
Page 197 and 198:
Page 199 and 200:
Page 201 and 202:
Page 203 and 204:
Page 205 and 206:
Page 207 and 208:
Page 209 and 210:
Page 211 and 212:
Page 213 and 214:
Page 215 and 216:
Page 217 and 218:
Page 219 and 220:
Page 221 and 222:
Page 223 and 224:
Page 225 and 226:
Page 227 and 228:
Page 229 and 230:
Page 231 and 232:
Page 233 and 234:
Page 235 and 236:
Page 237 and 238:
Page 239 and 240:
Page 241 and 242:
Page 243 and 244:
Page 245 and 246:
Page 247 and 248:
Page 249 and 250:
Page 251 and 252:
Page 253 and 254:
Page 255 and 256:
Page 257 and 258:
Page 259 and 260:
Page 261 and 262:
Page 263 and 264:
Page 265 and 266:
Page 267 and 268:
Page 269 and 270:
Page 271 and 272:
Page 273 and 274:
Page 275 and 276:
Page 277 and 278:
Page 279 and 280:
Page 281 and 282:
Page 283 and 284:
Page 285 and 286:
Page 287 and 288:
Page 289 and 290:
Page 291 and 292:
Page 293 and 294:
Page 295 and 296:
Page 297 and 298:
Page 299 and 300:
Page 301 and 302:
Page 303 and 304:
Page 305 and 306:
Page 307 and 308:
Page 309 and 310:
Page 311 and 312:
Page 313 and 314:
Page 315 and 316:
Page 317 and 318:
Page 319 and 320:
Page 321 and 322:
Page 323 and 324:
Page 325 and 326:
Page 327 and 328:
Page 329 and 330:
Page 331 and 332:
Page 333 and 334:
Page 335 and 336:
Page 337 and 338:
Page 339 and 340:
Page 341 and 342:
Page 343 and 344:
Page 345 and 346:
Page 347 and 348:
Page 349 and 350:
Page 351 and 352:
Page 353 and 354:
Page 355 and 356:
Page 357 and 358:
Page 359 and 360:
Page 361 and 362:
Page 363 and 364:
Page 365 and 366:
Page 367 and 368:
Page 369 and 370:
Page 371 and 372:
Page 373 and 374:
Page 375 and 376:
Page 377 and 378:
Page 379 and 380:
Page 381 and 382:
Page 383 and 384:
Page 385 and 386:
Page 387 and 388:
Page 389 and 390:
Page 391 and 392:
Page 393 and 394:
Page 395 and 396:
Page 397 and 398:
Page 399 and 400:
Page 401 and 402:
Page 403 and 404:
Page 405 and 406:
Page 407 and 408:
Page 409 and 410:
Page 411 and 412:
Page 413 and 414:
Page 415 and 416:
Page 417 and 418:
Page 419 and 420:
Page 421 and 422:
Page 423 and 424:
Page 425 and 426:
Page 427 and 428:
Page 429 and 430:
Page 431 and 432:
Page 433 and 434:
Page 435 and 436:
Page 437 and 438:
Page 439 and 440:
Page 441 and 442:
Page 443 and 444:
Page 445 and 446:
Page 447 and 448:
Page 449 and 450:
Page 451 and 452:
436 NITRONATES One of the processes
Page 453 and 454:
438 NITRONATES and E + are involved
Page 455 and 456:
440 NITRONATES C 6H 5CH(CN)NO 2 R
Page 457 and 458:
442 NITRONATES It should be noted t
Page 459 and 460:
444 NITRONATES AN () n Y X NO 2 A (
Page 461 and 462:
446 NITRONATES p-NO 2-C 6H 4 NO2 Br
Page 463 and 464:
448 NITRONATES MeO2CCH2NO2 11 RCHO
Page 465 and 466:
450 NITRONATES R 2 R 1 X 15 R 3 OH
Page 467 and 468:
452 NITRONATES RCOO OCOR + [PhSO2CH
Page 469 and 470:
454 NITRONATES M + [XC(NO 2) 2] −
Page 471 and 472:
456 NITRONATES NO2 CO2DBHA 23b R 1
Page 473 and 474:
458 NITRONATES NO2 R 1 Halogenation
Page 475 and 476:
460 NITRONATES R NO 2 R R' OH O N R
Page 477 and 478:
462 NITRONATES isomeric Þve-member
Page 479 and 480:
464 NITRONATES O N O 42 + Alk Alk A
Page 481 and 482:
466 NITRONATES R 1 Ph NO2 R 2 H + M
Page 483 and 484:
468 NITRONATES NO 2 O N NO2 O O N 4
Page 485 and 486:
470 NITRONATES R R′ C(NO 2)Si C N
Page 487 and 488:
472 NITRONATES R NO2 + Li2S LiHS +
Page 489 and 490:
474 NITRONATES (DMAP) provides the
Page 491 and 492:
476 NITRONATES Table 3.2 (continued
Page 493 and 494:
478 NITRONATES NO2 O EtO P X Me −
Page 495 and 496:
480 NITRONATES Table 3.4 The silyla
Page 497 and 498:
482 NITRONATES MeO X NO2 O O N O
Page 499 and 500:
484 NITRONATES O N OBR3 2 R 1 R 2 6
Page 501 and 502:
486 NITRONATES [CH 3CH=NO 2] − CH
Page 503 and 504:
488 NITRONATES R OBEt2O R' R N R N
Page 505 and 506:
490 NITRONATES R R′ R R′ O N H
Page 507 and 508:
492 NITRONATES Table 3.5 Physical c
Page 509 and 510:
Page 511 and 512:
Page 513 and 514:
498 NITRONATES The physicochemical
Page 515 and 516:
500 NITRONATES NO 2 CH 3 CH 3 OMe O
Page 517 and 518:
502 NITRONATES Nitronates, in which
Page 519 and 520:
504 NITRONATES Ha R′ Hb R′′ O
Page 521 and 522:
506 NITRONATES N-O bonds in nitrona
Page 523 and 524:
508 NITRONATES Me Me O O− N + A M
Page 525 and 526:
510 NITRONATES O CF 3 R O N H OSi t
Page 527 and 528:
512 NITRONATES EtOCO N(NO2)SiMe3 Et
Page 529 and 530:
514 NITRONATES O 98 N O OH HO O 99
Page 531 and 532:
516 NITRONATES 3.4. REACTIVITY OF N
Page 533 and 534:
518 NITRONATES N Nu E E Nu O OX OX
Page 535 and 536:
520 NITRONATES Two examples of succ
Page 537 and 538:
522 NITRONATES RSH 111 RSH + 111 R
Page 539 and 540:
524 NITRONATES SiO N O O MeO SAr Cl
Page 541 and 542:
526 NITRONATES Bu t Me 2SiO Me R N
Page 543 and 544:
528 NITRONATES (NO 2) 3C − Met +
Page 545 and 546:
530 NITRONATES 3.4.2.4. Dialkylbory
Page 547 and 548:
532 NITRONATES groups present as su
Page 549 and 550:
534 NITRONATES O N EtO EtO O O N KO
Page 551 and 552:
536 NITRONATES EtO 2C R 3 R 4 R 5 O
Page 553 and 554:
538 NITRONATES MeO2C BzO 2C MeO2C R
Page 555 and 556:
540 NITRONATES of the observed tran
Page 557 and 558:
542 NITRONATES R 2 = H R 1 = Me R 3
Page 559 and 560:
544 NITRONATES R 1 R 2 O N OR 3 + R
Page 561 and 562:
546 NITRONATES N R H OSi K 1 O O N
Page 563 and 564:
548 NITRONATES 3.4.3.1.2. Silyl Nit
Page 565 and 566:
550 NITRONATES HO CO 2Me Ref. 49, 9
Page 567 and 568:
552 NITRONATES OEt Ph + + OEt NO2 +
Page 569 and 570:
554 NITRONATES MeO MeO N O MeO N O
Page 571 and 572:
556 NITRONATES OSiMe2Bu O O N t H O
Page 573 and 574:
558 NITRONATES R PhCOCH 2SCH 2R 177
Page 575 and 576:
560 NITRONATES R 185 NO2 HX R′ R
Page 577 and 578:
562 NITRONATES References to Scheme
Page 579 and 580:
564 NITRONATES In addition to the g
Page 581 and 582:
566 NITRONATES OSiMe 3 + 203 MeO 20
Page 583 and 584:
568 NITRONATES Me 2Si R 1 R 2 R 1 R
Page 585 and 586:
570 NITRONATES Me Me Me Me O N (•
Page 587 and 588:
572 NITRONATES easily be cleaved. I
Page 589 and 590:
574 NITRONATES The process is initi
Page 591 and 592:
576 NITRONATES NO2 R O N 241 O R′
Page 593 and 594:
578 NITRONATES R′′O R′ R′ R
Page 595 and 596:
580 NITRONATES 3.4.3.4.4. Determina
Page 597 and 598:
582 NITRONATES N OR′ R O 247 H R
Page 599 and 600:
584 NITRONATES R′′Ο R′′Ο
Page 601 and 602:
586 NITRONATES Table 3.16 Stereoche
Page 603 and 604:
588 NITRONATES R 2 O R 1 OR 1 O N H
Page 605 and 606:
590 NITRONATES O O O N 2 O 1 3 4 25
Page 607 and 608:
592 NITRONATES O N O + D O N O 259
Page 609 and 610:
594 NITRONATES HO BH 3 − O O H OB
Page 611 and 612:
596 NITRONATES Two component [4+2]
Page 613 and 614:
598 NITRONATES O O OR R - (+)menthy
Page 615 and 616:
600 NITRONATES X O R Me 287 O O O N
Page 617 and 618:
602 NITRONATES Most studies and app
Page 619 and 620:
604 NITRONATES O2N O O N HN 302 OH
Page 621 and 622:
606 NITRONATES Hc H b NO2 314 Hc BH
Page 623 and 624:
608 NITRONATES R R′ NO 2 LiR′
Page 625 and 626:
610 NITRONATES SiO N O R 1 R 2 R 3
Page 627 and 628:
612 NITRONATES this scheme, SENAs h
Page 629 and 630:
614 NITRONATES SiO N O H R1 327 + R
Page 631 and 632:
616 NITRONATES Nu − R OSi N O 1 R
Page 633 and 634:
618 NITRONATES H NO2 Base (K 1) H
Page 635 and 636:
620 NITRONATES Table 3.18 Double si
Page 637 and 638:
622 NITRONATES SiO SiO N OSi R N OS
Page 639 and 640:
624 NITRONATES 342 or 342′ Si -tr
Page 641 and 642:
626 NITRONATES Table 3.20 The effec
Page 643 and 644:
628 NITRONATES by more than 1.5 ppm
Page 645 and 646:
630 NITRONATES R 1 R 2 O TfOH R 1 N
Page 647 and 648:
632 NITRONATES Table 3.23 The kinet
Page 649 and 650:
634 NITRONATES Two procedures were
Page 651 and 652:
636 NITRONATES Table 3.25 Stereoche
Page 653 and 654:
638 NITRONATES For example, carbony
Page 655 and 656:
640 NITRONATES MeO Me MeO Me MeO Me
Page 657 and 658:
642 NITRONATES Me3SiO O N CH A R 2
Page 659 and 660:
644 NITRONATES R 4 NO2 R 2 Me 3SiO
Page 661 and 662:
646 NITRONATES MeO Me 3SiO A MeO Me
Page 663 and 664:
648 NITRONATES R 1 R 2 R 1 R 2 R 1
Page 665 and 666:
650 NITRONATES (•) n CH3NO2 or Et
Page 667 and 668:
652 NITRONATES Y N O NO2 O 396 Y
Page 669 and 670:
654 NITRONATES E + + N OSi N OSi +
Page 671 and 672:
656 NITRONATES H G b R 2 H G β R 2
Page 673 and 674:
658 NITRONATES SiO N OSi OSi −
Page 675 and 676:
660 NITRONATES R = OSiMe2Bu-t noneq
Page 677 and 678:
662 NITRONATES Table 3.27 Some calc
Page 679 and 680:
664 NITRONATES Table 3.28 The barri
Page 681 and 682:
666 NITRONATES Table 3.29 The study
Page 683 and 684:
668 NITRONATES R 1 NO2 R 2 E E + R
Page 685 and 686:
670 NITRONATES Si - SiMe3 NO2 + N(O
Page 687 and 688:
672 NITRONATES Table 3.30 The appro
Page 689 and 690:
674 NITRONATES the silyl derivative
Page 691 and 692:
676 NITRONATES R 3 O − N 448 R 1
Page 693 and 694:
678 NITRONATES R 2 R 4 OC CHR 5 R3O
Page 695 and 696:
680 NITRONATES R 2 R 2 R 2 N H 434
Page 697 and 698:
682 NITRONATES R 2 R 1 R 3 NH2 N(OS
Page 699 and 700:
684 NITRONATES was reduced to form
Page 701 and 702:
686 NITRONATES O 2N R 1 R 2 R 2 R 3
Page 703 and 704:
688 NITRONATES R 3 X NH Y Z 471 N H
Page 705 and 706:
690 NITRONATES R 3 R5 R4 R 2 O N 47
Page 707 and 708:
692 NITRONATES Table 3.34 The coupl
Page 709 and 710:
694 NITRONATES MeO Me An An O N 489
Page 711 and 712:
696 NITRONATES R 497 N TBS - SiMe 2
Page 713 and 714:
698 NITRONATES R 1 N(OSiMe3)2 434 R
Page 715 and 716:
700 NITRONATES An O N MeO OSi Me 50
Page 717 and 718:
702 NITRONATES R 1 434 N(OSiMe3)2 R
Page 719 and 720:
704 NITRONATES The possibility of u
Page 721 and 722:
706 NITRONATES Table 3.36 The synth
Page 723 and 724:
708 NITRONATES compounds containing
Page 725 and 726:
710 NITRONATES [529] + [530] MeO2C
Page 727 and 728:
712 NITRONATES (539). However, α-m
Page 729 and 730:
714 NITRONATES Thus, the synthesis
Page 731 and 732:
716 NITRONATES However, if AN (562)
Page 733 and 734:
718 NITRONATES R 1 CH 2NO 2 R 2 CHO
Page 735 and 736:
720 NITRONATES O 2N Me3SiO 580a OSi
Page 737 and 738:
722 NITRONATES bubbling a solution
Page 739 and 740:
724 NITRONATES R 4 R 3 O + NO2 + R
Page 741 and 742:
726 NITRONATES NO 2 N H OMe O O O N
Page 743 and 744:
728 NITRONATES 13. Boyer JP, Manima
Page 745 and 746:
730 NITRONATES 65. Rosini G, Galari
Page 747 and 748:
732 NITRONATES 125. Felluda F, Nitt
Page 749 and 750:
734 NITRONATES 191. Dehaen W, Hassn
Page 751 and 752:
736 NITRONATES 247. Auvers KV, Ofte
Page 753 and 754:
738 NITRONATES 295. Clayden J, Gree
Page 755 and 756:
740 NITRONATES 353. Kamernitsky AV,
Page 757 and 758:
742 NITRONATES 407. Vorontsova LG.
Page 759 and 760:
744 NITRONATES 466. Dilman AD, Tish
Page 761 and 762:
746 NITRONATES 514. Ustinov AV, Dil
Page 764 and 765:
INDEX Allyl acetates, 451 Applicati
Page 766 and 767:
INDEX 751 Michael additions, 446, 4
Page 768:
INDEX 753 intermolecular cycloaddit
show all

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

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

Delete template?

Save as template?