Knowledge (XXG)

Dihydroimidazol-2-ylidene

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Although carbenes in general are extremely short-lived, some derivatives of this compound are surprisingly stable, and form an important class of the
591: 23: 596: 133: 555: 263: 354: 473: 548: 476:, H. V. R. Dias, R. L. Harlow, and M. Kline (1992). "Electronic stabilization of nucleophilic carbenes". 586: 528: 498: 295: 414: 388: 374: 318: 36: 419: 314: 74: 581: 478: 379: 94: 532: 486: 455: 428: 396: 279: 191: 392: 339:, a stable carbene without delocalization around the ring containing the carbenic carbon 342: 234: 575: 328:
Wanzlick's mechanism for the reaction of dihydroimidazol-2-ylidene with electrophiles
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with two hydrogen atoms removed from carbon number 2, leaving two vacant
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They also include an example of the (saturated) imidazolin-2-ylidene (
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H.-W. Wanzlick (1962). "Aspects of Nucleophilic Carbene Chemistry".
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Except where otherwise noted, data are given for materials in their
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and E. Schikora (1960). "Ein neuer Zugang zur Carben-Chemie".
536: 251: 417:and E. Schikora (1960). "Ein nucleophiles Carben". 118: 556: 8: 503:: CS1 maint: multiple names: authors list ( 337:1,3-Dimesityl-imidazol-4,5-dihydro-2-ylidene 563: 549: 93: 15: 142:InChI=1S/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 366: 173: 152:InChI=1/C3H6N2/c1-2-5-3-4-1/h4-5H,1-2H2 138: 496: 145:Key: JKQUEGZDRZXJNY-UHFFFAOYSA-N 7: 517: 515: 155:Key: JKQUEGZDRZXJNY-UHFFFAOYAT 109: 535:. You can help Knowledge (XXG) by 14: 519: 241: 209: 203: 22: 592:Hypothetical chemical compounds 237:(at 25 °C , 100 kPa). 197: 1: 597:Heterocyclic compound stubs 613: 514: 448:Angew. Chem. Int. Ed. Engl 17:Dihydroimidazol-2-ylidene 276:Dihydroimidazol-2-ylidene 231: 184: 164: 129: 55: 47: 35: 30: 21: 433:10.1002/cber.19610940905 401:10.1002/ange.19600721409 298:, formally derived from 460:10.1002/anie.196200751 346: 329: 41:Imidazolidin-2-ylidene 529:heterocyclic compound 527:This article about a 335: 327: 296:heterocyclic compound 415:Hans-Werner Wanzlick 319:Hans-Werner Wanzlick 37:Preferred IUPAC name 491:10.1021/ja00040a007 474:A. J. Arduengo, III 393:1960AngCh..72..494W 315:persistent carbenes 306:— which makes it a 227: g·mol 18: 420:Chemische Berichte 347: 330: 278:is a hypothetical 264:Infobox references 16: 544: 543: 485:(14): 5530–5534. 479:J. Am. Chem. Soc. 380:Angewandte Chemie 272:Chemical compound 270: 269: 75:Interactive image 604: 565: 558: 551: 523: 516: 509: 508: 502: 494: 470: 464: 463: 443: 437: 436: 427:(9): 2389–2393. 411: 405: 404: 371: 294:. It would be a 280:organic compound 254: 248: 245: 244: 226: 211: 205: 199: 192:Chemical formula 122: 111: 97: 77: 26: 19: 612: 611: 607: 606: 605: 603: 602: 601: 572: 571: 570: 569: 513: 512: 495: 472: 471: 467: 445: 444: 440: 413: 412: 408: 373: 372: 368: 363: 343:external viewer 340: 293: 289: 285: 273: 266: 261: 260: 259:  ?) 250: 246: 242: 238: 224: 214: 208: 202: 194: 180: 177: 172: 171: 160: 157: 156: 153: 147: 146: 143: 137: 136: 125: 112: 100: 80: 67: 51: 50:Diazolanylidene 43: 42: 12: 11: 5: 610: 608: 600: 599: 594: 589: 584: 574: 573: 568: 567: 560: 553: 545: 542: 541: 524: 511: 510: 465: 438: 406: 375:H.-W. Wanzlick 365: 364: 362: 359: 353:) reported by 304:chemical bonds 291: 287: 283: 282:with formula C 271: 268: 267: 262: 240: 239: 235:standard state 232: 229: 228: 222: 216: 215: 212: 206: 200: 195: 190: 187: 186: 182: 181: 179: 178: 175: 167: 166: 165: 162: 161: 159: 158: 154: 151: 150: 148: 144: 141: 140: 132: 131: 130: 127: 126: 124: 123: 115: 113: 105: 102: 101: 99: 98: 90: 88: 82: 81: 79: 78: 70: 68: 61: 58: 57: 53: 52: 49: 45: 44: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 609: 598: 595: 593: 590: 588: 585: 583: 580: 579: 577: 566: 561: 559: 554: 552: 547: 546: 540: 538: 534: 530: 525: 522: 518: 506: 500: 492: 488: 484: 481: 480: 475: 469: 466: 461: 457: 453: 449: 442: 439: 434: 430: 426: 422: 421: 416: 410: 407: 402: 398: 394: 390: 386: 382: 381: 376: 370: 367: 360: 358: 356: 355:A.J. Arduengo 352: 344: 338: 334: 326: 322: 321:around 1960. 320: 316: 311: 309: 305: 301: 300:imidazolidine 297: 281: 277: 265: 258: 253: 236: 230: 223: 221: 218: 217: 196: 193: 189: 188: 183: 174: 170: 163: 149: 139: 135: 128: 121: 117: 116: 114: 108: 104: 103: 96: 92: 91: 89: 87: 84: 83: 76: 72: 71: 69: 65: 60: 59: 54: 46: 38: 34: 29: 25: 20: 587:Imidazolines 537:expanding it 526: 499:cite journal 482: 477: 468: 454:(2): 75–80. 451: 447: 441: 424: 418: 409: 384: 378: 369: 348: 312: 275: 274: 56:Identifiers 48:Other names 387:(14): 494. 185:Properties 576:Categories 361:References 220:Molar mass 86:ChemSpider 62:3D model ( 357:in 1995. 582:Carbenes 120:60208178 95:11350507 389:Bibcode 351:carbene 308:carbene 257:what is 255: ( 107:PubChem 252:verify 249:  225:70.095 176:1NCCN1 169:SMILES 31:Names 531:is a 134:InChI 64:JSmol 533:stub 505:link 487:doi 483:114 456:doi 429:doi 397:doi 110:CID 578:: 501:}} 497:{{ 450:. 425:94 423:. 395:. 385:72 383:. 310:. 564:e 557:t 550:v 539:. 507:) 493:. 489:: 462:. 458:: 452:1 435:. 431:: 403:. 399:: 391:: 345:) 341:( 292:2 290:N 288:6 286:H 284:3 247:Y 213:2 210:N 207:6 204:H 201:3 198:C 66:)

Index

Skeletal formula of dihydroimidazol-2-ylidene
Preferred IUPAC name
JSmol
Interactive image
ChemSpider
11350507
PubChem
60208178
InChI
SMILES
Chemical formula
Molar mass
standard state
verify
what is
Infobox references
organic compound
heterocyclic compound
imidazolidine
chemical bonds
carbene
persistent carbenes
Hans-Werner Wanzlick


1,3-Dimesityl-imidazol-4,5-dihydro-2-ylidene
external viewer
carbene
A.J. Arduengo
H.-W. Wanzlick

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