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Borabenzene

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Boese, Roland; Finke, Norbert; Henkelmann, Jochem; Maier, Günther; Paetzold, Peter; Reisenauer, Hans Peter; Schmid, Günter (1985). "Synthese und Strukturuntersuchung von Pyridin-Borabenzol und Pyridin-2-Boranaphthalin".
457:. It is a yellow whereas biphenyl is colorless, indicating distinct electronic structures. The pyridine ligand is tightly bound: no exchange is observed with free pyridine, even at elevated temperatures. 313:
are isolatable. Since borabenzene is unavailable, these adducts require indirect methods. 4-Silyl-1-methoxyboracyclohexadiene is used as a precursor to the borabenzene:
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Wood, Thomas K.; Piers, Warren E.; Keay, Brian A.; Parvez, Masood (2006). "1-Borabarrelene Derivatives via Diels−Alder Additions to Borabenzenes".
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B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the
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6-membered aromatic rings with one carbon replaced by another group:
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Except where otherwise noted, data are given for materials in their
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Adducts of borabenzene with pyridine and triphenylphosphine.
150: 132: 472:The borabenzene-pyridine adduct behaves like a 63: 8: 107: 15: 567: 206: 181: 161: 188:Key: HXNZTJULPKRNPR-UHFFFAOYSA-N 7: 185:InChI=1S/C5H5B/c1-2-4-6-5-3-1/h1-5H 123: 14: 492: 236: 22: 654:Hypothetical chemical compounds 301:anions, including the parent . 267:(at 25 °C , 100 kPa). 230: 1: 242: 309:Adducts of borabenzene with 453:is structurally related to 670: 261: 217: 197: 172: 47: 35: 30: 21: 590:10.1002/cber.19851180431 467: 486:Diels-Alder reactions 465: 414:The pyridine adduct 287:organoboron compound 37:Preferred IUPAC name 484:, and will undergo 257: g·mol 18: 649:Six-membered rings 644:Boron heterocycles 578:Chemische Berichte 468: 289:with the formula C 285:is a hypothetical 271:Infobox references 16: 617:10.1021/ol061201w 611:(13): 2875–2878. 279:Chemical compound 277: 276: 146:CompTox Dashboard 89:Interactive image 661: 629: 628: 600: 594: 593: 584:(4): 1644–1654. 572: 496: 452: 451: 450: 442: 441: 433: 432: 424: 423: 406: 405: 404: 396: 395: 387: 386: 378: 377: 367: 366: 365: 357: 356: 348: 347: 337: 335: 334: 326: 325: 256: 244: 238: 232: 225:Chemical formula 165: 154: 152: 136: 125: 111: 91: 67: 26: 19: 669: 668: 664: 663: 662: 660: 659: 658: 634: 633: 632: 605:Organic Letters 602: 601: 597: 574: 573: 569: 565: 552:telluropyrylium 503: 449: 446: 445: 444: 440: 437: 436: 435: 431: 428: 427: 426: 422: 419: 418: 417: 415: 410: 403: 400: 399: 398: 394: 391: 390: 389: 385: 382: 381: 380: 376: 373: 372: 371: 369: 364: 361: 360: 359: 355: 352: 351: 350: 346: 343: 342: 341: 339: 333: 330: 329: 328: 324: 321: 320: 319: 317: 307: 296: 292: 280: 273: 268: 254: 241: 235: 227: 213: 210: 205: 204: 193: 190: 189: 186: 180: 179: 168: 155: 148: 139: 126: 114: 94: 81: 70: 57: 43: 42: 12: 11: 5: 667: 665: 657: 656: 651: 646: 636: 635: 631: 630: 595: 566: 564: 561: 560: 559: 554: 548:selenopyrylium 502: 499: 498: 497: 470: 469: 447: 438: 429: 420: 412: 411: 408: 401: 392: 383: 374: 362: 353: 344: 331: 322: 306: 303: 294: 290: 278: 275: 274: 269: 265:standard state 262: 259: 258: 252: 246: 245: 239: 233: 228: 223: 220: 219: 215: 214: 212: 211: 208: 200: 199: 198: 195: 194: 192: 191: 187: 184: 183: 175: 174: 173: 170: 169: 167: 166: 163:DTXSID50447608 158: 156: 144: 141: 140: 138: 137: 129: 127: 119: 116: 115: 113: 112: 104: 102: 96: 95: 93: 92: 84: 82: 75: 72: 71: 69: 68: 60: 58: 53: 50: 49: 45: 44: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 666: 655: 652: 650: 647: 645: 642: 641: 639: 626: 622: 618: 614: 610: 606: 599: 596: 591: 587: 583: 579: 571: 568: 562: 558: 555: 553: 549: 545: 541: 537: 533: 529: 525: 521: 517: 516:stannabenzene 513: 509: 505: 504: 500: 495: 491: 490: 489: 487: 483: 479: 475: 464: 460: 459: 458: 456: 316: 315: 314: 312: 304: 302: 300: 299:boratabenzene 288: 284: 272: 266: 260: 253: 251: 248: 247: 229: 226: 222: 221: 216: 207: 203: 196: 182: 178: 171: 164: 160: 159: 157: 147: 143: 142: 135: 131: 130: 128: 122: 118: 117: 110: 106: 105: 103: 101: 98: 97: 90: 86: 85: 83: 79: 74: 73: 66: 62: 61: 59: 56: 52: 51: 46: 38: 34: 29: 25: 20: 608: 604: 598: 581: 577: 570: 544:thiopyrylium 536:bismabenzene 532:stibabenzene 512:germabenzene 471: 413: 308: 282: 281: 48:Identifiers 17:Borabenzene 528:arsabenzene 524:phosphorine 508:silabenzene 311:Lewis bases 283:Borabenzene 218:Properties 209:B1=CC=CC=C1 638:Categories 563:References 250:Molar mass 100:ChemSpider 76:3D model ( 65:31029-61-5 55:CAS Number 476:, not an 407:+ MeOSiMe 625:16774279 557:Borazine 540:pyrylium 520:pyridine 501:See also 482:biphenyl 455:biphenyl 134:10899214 41:Borinine 305:Adducts 121:PubChem 109:9074474 623:  478:analog 202:SMILES 31:Names 474:diene 340:MeOBC 255:75.91 177:InChI 78:JSmol 621:PMID 434:N-BC 388:N-BC 358:SiMe 613:doi 586:doi 582:118 480:of 151:EPA 124:CID 640:: 619:. 607:. 580:. 550:, 546:, 542:, 538:, 534:, 530:, 526:, 522:, 518:, 514:, 510:, 488:. 368:→ 338:+ 627:. 615:: 609:8 592:. 588:: 448:5 443:H 439:5 430:5 425:H 421:5 416:C 409:3 402:5 397:H 393:5 384:5 379:H 375:5 370:C 363:3 354:5 349:H 345:5 336:N 332:5 327:H 323:5 318:C 295:5 293:H 291:5 243:B 240:5 237:H 234:5 231:C 153:) 149:( 80:)

Index


Preferred IUPAC name
CAS Number
31029-61-5
JSmol
Interactive image
ChemSpider
9074474
PubChem
10899214
CompTox Dashboard
DTXSID50447608
InChI
SMILES
Chemical formula
Molar mass
standard state
Infobox references
organoboron compound
boratabenzene
Lewis bases
biphenyl

diene
analog
biphenyl
Diels-Alder reactions
Borabarrelene synthesis via a Diels-Alder reaction of borabenzene-pyridine adduct
silabenzene
germabenzene

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