674:
550:
760:
290:
that many potential workers in this field have been turned away by the odour, but this is heavily outweighed by the fact that isonitriles can be detected even in traces, and that most of the routes leading to the formation of isonitriles were discovered through the odor of these compounds." Isocyanides have been investigated as potential
233:
between. The π lone pair of the nitrogen stabilizes the structure and is responsible of the linearity of isocyanides, although the reactivity of isocyanides reflects some carbene character, at least in a formal sense. Thus, both resonance structures are useful representations. They are susceptible to
289:
states that "The development of the chemistry of isocyanides has probably suffered only little delay through the characteristic odor of volatile isonitriles, which has been described by
Hofmann and Gautier as 'highly specific, almost overpowering', 'horrible', and 'extremely distressing'. It is true
313:
cyclohexyl isocyanide) are toxic, others "exhibit no appreciable toxicity for mammals". Referring to ethyl isocyanide, toxicological studies in the 1960s at Bayer showed that "oral and subcutaneous doses of 500-5000 mg/kg can be tolerated by mice".
564:
Isocyanides are stable to strong base (they are often made under strongly basic conditions), but they are sensitive to acid. In the presence of aqueous acid, isocyanides hydrolyse to the corresponding
754:. Since then numerous other isocyanides have been isolated. Most of the marine isocyanides are terpenoid, while some of the terrestrial isocyanides originate from α-aminoacids.
140:
803:
functional group consists of an amino group attached to an isocyano moiety. The isonitrile suffix or isocyano- prefix is used depending upon priority table.
1692:
619:
Isocyanides have also been shown to be a useful reagent in palladium catalysed reactions with a wide variety of compounds being formed using this method.
608:
reactions, such as the cycloaddition with tetrazines. Depending on the degree of substitution of the isocyanide, this reaction converts isocyanides into
2611:
979:
1081:
2616:
1389:
Imming, P.; R. Mohr; E. Müller; W. Overheu; G. Seitz (1982). "Cycloaddition of
Isocyanides to 1,2,4,5-Tetrazines: A Novel Synthesis of Pyrazole".
1196:
Siobhan
Creedon; H. Kevin Crowley; Daniel G. McCarthy (1998). "Dehydration of formamides using the Burgess Reagent: a new route to isocyanides".
1416:
Stöckmann, H.; A. Neves; S. Stairs; K. Brindle; F. Leeper (2011). "Exploring
Isonitrile-Based Click Chemistry for Ligation with Biomolecules".
880:
Kessler, M.; Ring, H.; Trambarulo, R.; Gordy, W. (1950). "Microwave
Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide".
918:
Ramozzi, R.; Chéron, N.; Braïda, B.; Hiberty, P. C.; Fleurat-Lessard, P. (2012). "A Valence Bond View of
Isocyanides' Electronic Structure".
668:
582:
This reaction is used to destroy odorous isocyanide mixtures. Some isocyanides can polymerize in the presence of Lewis and
Bronsted acids.
297:
Some isocyanides convey less offensive odours such as malt, natural rubber, creosote, cherry or old wood. Non-volatile derivatives such as
1115:
B. E. Hoogenboom, O. H. Oldenziel, and A. M. van Leusen "Toluenesulfonylmethyl isocyanide" Organic
Syntheses, Coll. Vol. 6, p.987 (1988).
740:
Only few naturally occurring compounds exhibit the isocyanide functionality. The first was discovered in 1957 in an extract of the mold
1584:
Bassett, J.M.; Barker, G.K.; Green, M.; Howard, J.A.; Stone, G.A.; Wolsey, W.C. "Chemistry of low-valent metal isocyanide complexes".
1568:
1512:
Filley, Jonathan; DePuy, Charles H.; Bierbaum, Veronica M. (1987-09-01). "Gas-phase negative-ion chemistry of methyl isocyanide".
1685:
1198:
2515:
1636:
948:
Stephany, R. W.; de Bie, M. J. A.; Drenth, W. (1974). "A C-NMR and IR study of isocyanides and some of their complexes".
1221:
Basoccu, Francesco; Cuccu, Federico; Casti, Federico; Mocci, Rita; Fattuoni, Claudia; Porcheddu, Andrea (22 June 2022).
1335:
G. W. Gokel; R. P. Widera; W. P. Weber (1988). "Phase-transfer
Hofmann Carbylamine Reaction: tert-Butyl Isocyanide".
261:
5 Hz for the isocyanide C nucleus and 5–14 Hz for the C nucleus which the isocyanide group is attached to.
2644:
2088:
1678:
1362:
Deming, T. J.; Novak, B. M. (1993). "Mechanistic
Studies on the Nickel Catalyzed Polymerization of Isocyanides".
1041:
Pirrung, M. C.; Ghorai, S.; Ibarra-Rivera, T. R. (2009). "Multicomponent Reactions of Convertible Isonitriles".
2125:
1453:
339:
2598:
613:
586:
452:
273:
Es besitzt einen penetranten, höchst unangenehmen Geruch; das Oeffnen eines Gefässes mit Cyanallyl [
2498:
343:
298:
283:...." Note that in Lieke's day, the difference between isocyanide and nitrile was not fully appreciated.
2605:
2493:
689:
656:
222:
145:
612:
or gives stable cycloadducts. They also undergo insertion into the C–Cl bonds of acyl chlorides in the
2639:
2574:
2019:
1451:
Lang, S. (2013). "Unravelling the labyrinth of palladium catalysed reactions involving isocyanides".
1170:
889:
685:
677:
531:
421:
331:
688:
with most transition metals. They behave as electron-rich analogues of carbon monoxide. For example
1880:
742:
598:
796:
always has three single bonds, whereas an isocyanide has only one single and one multiple bond.
714:. Although structurally similar, the analogous carbonyls differ in several ways, mainly because
549:
246:
Isocyanides exhibit a strong absorption in their IR spectra in the range of 2165–2110 cm.
2564:
2534:
2292:
1914:
1564:
1529:
1470:
1433:
1254:
1161:
1126:
1098:
1058:
862:
622:
The α position of isocyanides have substantial acidity. For example, benzyl isocyanide has a p
590:
291:
211:
1014:
Ugi, I.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. (1965). "Isonitrile Syntheses".
2269:
1763:
1701:
1645:
1616:
1556:
1521:
1462:
1425:
1398:
1371:
1344:
1317:
1285:
1244:
1234:
1203:
1178:
1138:
1090:
1050:
1023:
993:
957:
927:
897:
852:
409:
250:
170:
166:
1662:
673:
2488:
2247:
2242:
2225:
2208:
2009:
1758:
984:
800:
786:
767:
441:
429:
405:
355:
218:
41:
1274:"A Practical and Convenient Procedure for the N-Formylation of Amines Using Formic Acid"
1174:
893:
2559:
2554:
2430:
2425:
2420:
2213:
2180:
1964:
1946:
1936:
1249:
1222:
506:
235:
1560:
616:, a process that is believed to be concerted and illustrates their carbene character.
2633:
2579:
2527:
2458:
2344:
2334:
2329:
2319:
2314:
2264:
2259:
2175:
2170:
2160:
2014:
1969:
1931:
1919:
1890:
1768:
1156:
792:
The sometimes used old term "carbylamine" conflicts with systematic nomenclature. An
605:
543:
486:
286:
249:
The electronic symmetry about the isocyanide N nucleus results in a slow quadrupolar
2510:
2397:
2392:
2369:
2120:
1959:
1885:
1822:
1817:
1795:
1751:
1736:
1726:
1604:
1079:
Pirrung, M. C.; Ghorai, S. (2006). "Versatile, Fragrant, Convertible Isonitriles".
763:
747:
594:
539:
502:
1488:
2569:
2522:
2483:
2364:
2252:
2237:
2232:
2220:
1785:
1780:
1746:
1741:
1731:
1709:
527:
401:
400:
The formamide precursors are, in turn, prepared from amines by formylation with
230:
226:
1290:
1273:
497:
Of historical interest but not often of practical value, the first isocyanide,
2478:
2469:
2349:
2304:
2200:
2165:
2095:
2031:
1954:
1902:
751:
565:
425:
351:
254:
31:
1547:
Singleton, Eric; Oosthuizen, Hester E. (1983). "Metal Isocyanide Complexes".
1533:
1348:
1321:
1182:
1142:
997:
866:
2445:
2359:
2324:
2309:
2297:
2140:
2115:
1924:
1305:
839:
Patil, Pravin; Ahmadian-Moghaddam, Maryam; Dömling, Alexander (2020-09-29).
448:
335:
1474:
1437:
1402:
1258:
1102:
1062:
1027:
961:
485:
As it is only effective for primary amines, this reaction can be used as a
901:
17:
2453:
2407:
2374:
2070:
1976:
1850:
1805:
1790:
1620:
609:
424:(also known as the Hofmann isocyanide synthesis) alkali base reacts with
347:
197:. They are used as building blocks for the synthesis of other compounds.
190:
1649:
1525:
1375:
820:
759:
680:
is a commercial isocyanide complex that is used in medicine for imaging.
189:. The organic fragment is connected to the isocyanide group through the
2415:
2339:
2190:
2185:
2150:
2135:
2130:
2100:
2083:
1907:
1834:
1800:
1634:
Scheuer, P. J. (1992). "Isocyanides and Cyanides as Natural Products".
1466:
1429:
1239:
931:
857:
840:
523:
279:] reicht hin, die Luft eines Zimmers mehrere Tage lang zu verpesten
182:
1094:
1054:
548:
2503:
2435:
2279:
1988:
1981:
1875:
1856:
1845:
1829:
1775:
1207:
782:
194:
178:
1670:
2384:
2354:
2287:
2145:
2110:
2105:
2078:
2026:
1993:
1897:
1721:
1607:(1980). "Notes. Protonation of pentakis(t-butyl isocyanide)iron".
793:
672:
530:
in the 2-position. The resulting organolithium compound exists in
498:
433:
269:
Isocyanides have a very disagreeable odour. Lieke remarked that "
1812:
1674:
1663:
IUPAC Nomenclature of Organic Compounds (Recommendations 1993)
275:
1159:; R. Meyr (1958). "Neue Darstellungsmethode für Isonitrile".
358:
in the presence of a base such as pyridine or triethylamine.
785:"isocyano" for the systematic nomenclature of isocyanides:
522:
Another route to isocyanides entails deprotonation of
44:
1609:
Journal of the Chemical Society, Dalton Transactions
1586:
Journal of the Chemical Society, Dalton Transactions
1223:"A trustworthy mechanochemical route to isocyanides"
2547:
2467:
2444:
2406:
2383:
2278:
2199:
2069:
2046:
2002:
1945:
1868:
1843:
1708:
408:of alkenes (and other sources of carbocations) and
229:between the nitrogen and the carbon and one with a
134:
436:to isocyanides. Illustrative is the synthesis of
322:Many routes to isocyanides have been developed.
27:Chemical compound with isocyanide group (-N+≡C-)
210:The C-N distance in isocyanides is 115.8 pm in
943:
941:
725:is easily protonated, whereas its counterpart
718:-BuNC is a better donor ligand than CO. Thus,
629:of 27.4. In comparison, benzyl cyanide has a p
1686:
1074:
1072:
913:
911:
8:
1272:정선호; 안진희; Park, Sang-Kyu; 최중권 (2002-01-20).
501:isocyanide, was prepared by the reaction of
270:
257:can be observed, with coupling constants of
2066:
1865:
1693:
1679:
1671:
1289:
1248:
1238:
1009:
1007:
856:
330:Commonly, isocyanides are synthesized by
121:
113:
102:
101:
96:
89:
85:
75:
69:
68:
58:
50:
43:
1514:Journal of the American Chemical Society
1082:Journal of the American Chemical Society
789:, isocyanoethane, isocyanopropane, etc.
758:
728:
721:
710:
706:
699:
695:
647:
639:
574:
477:
473:
469:
465:
461:
404:or formyl acetyl anhydride, or from the
392:
388:
384:
380:
376:
372:
368:
364:
1391:Angewandte Chemie International Edition
1278:Bulletin of the Korean Chemical Society
1016:Angewandte Chemie International Edition
973:
971:
834:
832:
830:
812:
338:. The formamide can be dehydrated with
1489:"Bordwell pKa Table (Acidity in DMSO)"
1227:Beilstein Journal of Organic Chemistry
669:Transition metal isocyanide complexes
561:Isocyanides have diverse reactivity.
7:
1549:Advances in Organometallic Chemistry
1418:Organic & Biomolecular Chemistry
1125:R. E. Schuster; J. E. Scott (1966).
770:that contains two isocyanide groups.
432:. The carbene then converts primary
221:, isocyanides are described by two
655:Chlorination of isocyanides gives
214:. The C-N-C angles are near 180°.
25:
1603:Bassett, J.-M.; Farrugia, L. J.;
663:Ligands in coordination chemistry
644:is 1.8 kcal/mol less acidic than
455:benzyltriethylammonium chloride.
1043:The Journal of Organic Chemistry
985:Annalen der Chemie und Pharmacie
604:Isocyanides also participate in
585:Isocyanides participate in many
1306:"a,b-DIMETHYL-b-PHENETHYLAMINE"
736:Naturally occurring isocyanides
1199:J. Chem. Soc., Perkin Trans. 1
538:, which can be captured by an
90:
1:
1637:Accounts of Chemical Research
1561:10.1016/S0065-3055(08)60404-9
185:(–C≡N), hence the prefix is
636:of 21.9. In the gas phase,
2661:
1291:10.5012/BKCS.2002.23.1.149
950:Organic Magnetic Resonance
666:
148:structure of an isocyanide
29:
2588:
271:
253:so that C-N nuclear spin
1454:Chemical Society Reviews
1349:10.15227/orgsyn.055.0096
1322:10.15227/orgsyn.044.0044
1183:10.1002/ange.19580702213
1143:10.15227/orgsyn.046.0075
998:10.1002/jlac.18591120307
920:New Journal of Chemistry
703:, which is analogous to
593:, two of which are: the
587:multicomponent reactions
340:toluenesulfonyl chloride
309:While some isocyanides (
30:Not to be confused with
2599:chemical classification
614:Nef isocyanide reaction
453:phase transfer catalyst
440:-butyl isocyanide from
1403:10.1002/anie.198202841
1028:10.1002/anie.196504721
962:10.1002/mrc.1270060112
771:
686:coordination complexes
681:
657:isocyanide dichlorides
553:
344:phosphorus oxychloride
299:tosylmethyl isocyanide
136:
2606:chemical nomenclature
902:10.1103/PhysRev.79.54
762:
750:later was used as an
690:tert-butyl isocyanide
676:
552:
513:RI + AgCN → RNC + AgI
301:do not have an odor.
206:Structure and bonding
137:
135:{\displaystyle \left}
1621:10.1039/DT9800001789
980:"Über das Cyanallyl"
678:Technetium sestamibi
532:chemical equilibrium
493:Silver cyanide route
489:for their presence.
422:carbylamine reaction
416:From dichlorocarbene
223:resonance structures
42:
2062:not C, H or O)
1650:10.1021/ar00022a001
1526:10.1021/ja00254a017
1376:10.1021/ja00073a028
1175:1958AngCh..70..702U
1127:"Methyl isocyanide"
1089:(36): 11772–11773.
894:1950PhRv...79...54K
743:Penicillium notatum
536:2-isocyanophenolate
447:in the presence of
2504:Hypervalent iodine
1467:10.1039/C3CS60022J
1430:10.1039/C1OB06424J
1240:10.3762/bjoc.18.73
1169:(22–23): 702–703.
932:10.1039/C2NJ40050B
858:10.1039/D0GC02722G
772:
682:
599:Passerini reaction
554:
476:CNC + 3 NaCl + 3 H
375:N → RNC + [C
292:non-lethal weapons
193:atom, not via the
132:
2645:Functional groups
2627:
2626:
2565:Sulfenyl chloride
2543:
2542:
2042:
2041:
1861:(only C, H and O)
1702:Functional groups
1520:(20): 5992–5995.
1493:www.chem.wisc.edu
1461:(12): 4867–4880.
1424:(21): 7303–7305.
1337:Organic Syntheses
1310:Organic Syntheses
1162:Angewandte Chemie
1131:Organic Syntheses
1095:10.1021/ja0644374
1055:10.1021/jo900414n
1049:(11): 4110–4117.
978:W. Lieke (1859).
851:(20): 6902–6911.
684:Isocyanides form
591:organic synthesis
212:methyl isocyanide
120:
110:
106:
95:
83:
79:
66:
62:
53:
16:(Redirected from
2652:
2594:
2499:Trifluoromethoxy
2067:
2063:
1866:
1862:
1715:
1695:
1688:
1681:
1672:
1665:
1660:
1654:
1653:
1631:
1625:
1624:
1615:(9): 1789–1790.
1600:
1594:
1593:
1581:
1575:
1574:
1544:
1538:
1537:
1509:
1503:
1502:
1500:
1499:
1485:
1479:
1478:
1448:
1442:
1441:
1413:
1407:
1406:
1386:
1380:
1379:
1364:J. Am. Chem. Soc
1359:
1353:
1352:
1332:
1326:
1325:
1302:
1296:
1295:
1293:
1269:
1263:
1262:
1252:
1242:
1218:
1212:
1211:
1208:10.1039/a708081f
1202:(6): 1015–1018.
1193:
1187:
1186:
1153:
1147:
1146:
1122:
1116:
1113:
1107:
1106:
1076:
1067:
1066:
1038:
1032:
1031:
1011:
1002:
1001:
975:
966:
965:
945:
936:
935:
926:(5): 1137–1340.
915:
906:
905:
877:
871:
870:
860:
841:"Isocyanide 2.0"
836:
825:
817:
731:
724:
713:
702:
651:
643:
578:
481:
410:hydrogen cyanide
396:
282:
281:
176:
171:functional group
167:organic compound
141:
139:
138:
133:
131:
127:
126:
125:
118:
117:
112:
111:
104:
103:
100:
93:
84:
77:
76:
74:
73:
67:
60:
59:
54:
51:
21:
2660:
2659:
2655:
2654:
2653:
2651:
2650:
2649:
2630:
2629:
2628:
2623:
2592:
2584:
2539:
2494:Trichloromethyl
2489:Trifluoromethyl
2463:
2440:
2402:
2379:
2274:
2243:Phosphine oxide
2195:
2061:
2059:
2058:
2056:
2054:
2052:
2050:
2048:
2038:
1998:
1941:
1860:
1859:
1854:
1849:
1839:
1713:
1712:
1704:
1699:
1669:
1668:
1661:
1657:
1644:(10): 433–439.
1633:
1632:
1628:
1602:
1601:
1597:
1583:
1582:
1578:
1571:
1546:
1545:
1541:
1511:
1510:
1506:
1497:
1495:
1487:
1486:
1482:
1450:
1449:
1445:
1415:
1414:
1410:
1388:
1387:
1383:
1361:
1360:
1356:
1334:
1333:
1329:
1304:
1303:
1299:
1271:
1270:
1266:
1220:
1219:
1215:
1195:
1194:
1190:
1155:
1154:
1150:
1124:
1123:
1119:
1114:
1110:
1078:
1077:
1070:
1040:
1039:
1035:
1013:
1012:
1005:
977:
976:
969:
947:
946:
939:
917:
916:
909:
882:Physical Review
879:
878:
874:
845:Green Chemistry
838:
837:
828:
819:IUPAC Goldbook
818:
814:
809:
787:isocyanomethane
781:IUPAC uses the
779:
768:natural product
746:. The compound
738:
730:
726:
723:
719:
712:
708:
704:
701:
697:
693:
671:
665:
649:
645:
641:
637:
635:
628:
589:of interest in
576:
572:
559:
520:
495:
479:
475:
471:
467:
463:
459:
430:dichlorocarbene
418:
406:Ritter reaction
394:
390:
386:
382:
378:
374:
370:
366:
363:RNHC(O)H + ArSO
362:
356:Burgess reagent
328:
326:From formamides
320:
307:
267:
244:
219:carbon monoxide
208:
203:
181:of the related
174:
151:
150:
149:
142:
49:
45:
40:
39:
35:
28:
23:
22:
15:
12:
11:
5:
2658:
2656:
2648:
2647:
2642:
2632:
2631:
2625:
2624:
2622:
2621:
2620:
2619:
2614:
2602:
2595:
2589:
2586:
2585:
2583:
2582:
2580:Sulfinylamines
2577:
2572:
2567:
2562:
2560:Phosphoramides
2557:
2555:Isothiocyanate
2551:
2549:
2545:
2544:
2541:
2540:
2538:
2537:
2532:
2531:
2530:
2520:
2519:
2518:
2508:
2507:
2506:
2501:
2496:
2491:
2486:
2475:
2473:
2465:
2464:
2462:
2461:
2456:
2450:
2448:
2442:
2441:
2439:
2438:
2433:
2431:Selenenic acid
2428:
2426:Seleninic acid
2423:
2421:Selenonic acid
2418:
2412:
2410:
2404:
2403:
2401:
2400:
2395:
2389:
2387:
2381:
2380:
2378:
2377:
2372:
2367:
2362:
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2317:
2312:
2307:
2302:
2301:
2300:
2290:
2284:
2282:
2276:
2275:
2273:
2272:
2267:
2262:
2257:
2256:
2255:
2245:
2240:
2235:
2230:
2229:
2228:
2218:
2217:
2216:
2214:Phosphodiester
2205:
2203:
2197:
2196:
2194:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2133:
2128:
2123:
2118:
2113:
2108:
2103:
2098:
2093:
2092:
2091:
2086:
2075:
2073:
2064:
2060:(one element,
2044:
2043:
2040:
2039:
2037:
2036:
2035:
2034:
2024:
2023:
2022:
2017:
2006:
2004:
2000:
1999:
1997:
1996:
1991:
1986:
1985:
1984:
1974:
1973:
1972:
1967:
1962:
1951:
1949:
1943:
1942:
1940:
1939:
1937:Methylenedioxy
1934:
1929:
1928:
1927:
1922:
1912:
1911:
1910:
1905:
1895:
1894:
1893:
1883:
1878:
1872:
1870:
1863:
1841:
1840:
1838:
1837:
1832:
1827:
1826:
1825:
1820:
1810:
1809:
1808:
1803:
1798:
1793:
1788:
1783:
1773:
1772:
1771:
1766:
1756:
1755:
1754:
1749:
1744:
1739:
1734:
1729:
1718:
1716:
1714:(only C and H)
1706:
1705:
1700:
1698:
1697:
1690:
1683:
1675:
1667:
1666:
1655:
1626:
1595:
1576:
1569:
1539:
1504:
1480:
1443:
1408:
1381:
1354:
1327:
1297:
1284:(1): 149–150.
1264:
1213:
1188:
1148:
1117:
1108:
1068:
1033:
1022:(6): 472–484.
1003:
992:(3): 316–321.
967:
937:
907:
872:
826:
811:
810:
808:
805:
778:
775:
774:
773:
737:
734:
667:Main article:
664:
661:
633:
626:
580:
579:
558:
555:
519:
516:
515:
514:
507:silver cyanide
494:
491:
483:
482:
451:amount of the
417:
414:
398:
397:
327:
324:
319:
316:
306:
303:
266:
263:
243:
240:
236:polymerization
207:
204:
202:
199:
143:
130:
124:
116:
109:
99:
92:
88:
82:
72:
65:
57:
48:
38:
37:
36:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2657:
2646:
2643:
2641:
2638:
2637:
2635:
2618:
2615:
2613:
2610:
2609:
2608:
2607:
2603:
2601:
2600:
2596:
2591:
2590:
2587:
2581:
2578:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2552:
2550:
2546:
2536:
2533:
2529:
2526:
2525:
2524:
2521:
2517:
2514:
2513:
2512:
2509:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2481:
2480:
2477:
2476:
2474:
2472:
2471:
2466:
2460:
2459:Telluroketone
2457:
2455:
2452:
2451:
2449:
2447:
2443:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2414:
2413:
2411:
2409:
2405:
2399:
2396:
2394:
2391:
2390:
2388:
2386:
2382:
2376:
2373:
2371:
2368:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2345:Sulfonic acid
2343:
2341:
2338:
2336:
2335:Sulfinic acid
2333:
2331:
2330:Thiosulfonate
2328:
2326:
2323:
2321:
2320:Thiosulfinate
2318:
2316:
2315:Sulfenic acid
2313:
2311:
2308:
2306:
2303:
2299:
2296:
2295:
2294:
2291:
2289:
2286:
2285:
2283:
2281:
2277:
2271:
2270:Phosphaallene
2268:
2266:
2265:Phosphaalkyne
2263:
2261:
2260:Phosphaalkene
2258:
2254:
2251:
2250:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2227:
2224:
2223:
2222:
2219:
2215:
2212:
2211:
2210:
2207:
2206:
2204:
2202:
2198:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2119:
2117:
2114:
2112:
2109:
2107:
2104:
2102:
2099:
2097:
2094:
2090:
2087:
2085:
2082:
2081:
2080:
2077:
2076:
2074:
2072:
2068:
2065:
2045:
2033:
2030:
2029:
2028:
2025:
2021:
2018:
2016:
2013:
2012:
2011:
2008:
2007:
2005:
2001:
1995:
1992:
1990:
1987:
1983:
1980:
1979:
1978:
1975:
1971:
1968:
1966:
1963:
1961:
1958:
1957:
1956:
1953:
1952:
1950:
1948:
1944:
1938:
1935:
1933:
1932:Ethylenedioxy
1930:
1926:
1923:
1921:
1918:
1917:
1916:
1913:
1909:
1906:
1904:
1901:
1900:
1899:
1896:
1892:
1889:
1888:
1887:
1884:
1882:
1879:
1877:
1874:
1873:
1871:
1867:
1864:
1858:
1852:
1847:
1842:
1836:
1833:
1831:
1828:
1824:
1821:
1819:
1816:
1815:
1814:
1811:
1807:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1784:
1782:
1779:
1778:
1777:
1774:
1770:
1767:
1765:
1762:
1761:
1760:
1757:
1753:
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1724:
1723:
1720:
1719:
1717:
1711:
1707:
1703:
1696:
1691:
1689:
1684:
1682:
1677:
1676:
1673:
1664:
1659:
1656:
1651:
1647:
1643:
1639:
1638:
1630:
1627:
1622:
1618:
1614:
1610:
1606:
1605:Stone, F.G.A.
1599:
1596:
1591:
1587:
1580:
1577:
1572:
1570:9780120311224
1566:
1562:
1558:
1554:
1550:
1543:
1540:
1535:
1531:
1527:
1523:
1519:
1515:
1508:
1505:
1494:
1490:
1484:
1481:
1476:
1472:
1468:
1464:
1460:
1456:
1455:
1447:
1444:
1439:
1435:
1431:
1427:
1423:
1419:
1412:
1409:
1404:
1400:
1396:
1392:
1385:
1382:
1377:
1373:
1369:
1365:
1358:
1355:
1350:
1346:
1342:
1338:
1331:
1328:
1323:
1319:
1315:
1311:
1307:
1301:
1298:
1292:
1287:
1283:
1279:
1275:
1268:
1265:
1260:
1256:
1251:
1246:
1241:
1236:
1232:
1228:
1224:
1217:
1214:
1209:
1205:
1201:
1200:
1192:
1189:
1184:
1180:
1176:
1172:
1168:
1164:
1163:
1158:
1157:Ivar Karl Ugi
1152:
1149:
1144:
1140:
1136:
1132:
1128:
1121:
1118:
1112:
1109:
1104:
1100:
1096:
1092:
1088:
1084:
1083:
1075:
1073:
1069:
1064:
1060:
1056:
1052:
1048:
1044:
1037:
1034:
1029:
1025:
1021:
1017:
1010:
1008:
1004:
999:
995:
991:
987:
986:
981:
974:
972:
968:
963:
959:
955:
951:
944:
942:
938:
933:
929:
925:
921:
914:
912:
908:
903:
899:
895:
891:
887:
883:
876:
873:
868:
864:
859:
854:
850:
846:
842:
835:
833:
831:
827:
824:
823:
816:
813:
806:
804:
802:
797:
795:
790:
788:
784:
776:
769:
765:
761:
757:
756:
755:
753:
749:
745:
744:
735:
733:
717:
691:
687:
679:
675:
670:
662:
660:
658:
653:
632:
625:
620:
617:
615:
611:
607:
606:cycloaddition
602:
600:
596:
592:
588:
583:
571:
570:
569:
567:
562:
556:
551:
547:
545:
544:acid chloride
541:
537:
533:
529:
525:
518:Other methods
517:
512:
511:
510:
508:
504:
500:
492:
490:
488:
487:chemical test
472:+ 3 NaOH → Me
458:
457:
456:
454:
450:
446:
444:
439:
435:
431:
427:
423:
415:
413:
411:
407:
403:
361:
360:
359:
357:
353:
349:
345:
341:
337:
333:
325:
323:
317:
315:
312:
304:
302:
300:
295:
293:
288:
287:Ivar Karl Ugi
284:
280:
277:
274:
264:
262:
260:
256:
252:
247:
241:
239:
237:
232:
228:
225:, one with a
224:
220:
215:
213:
205:
200:
198:
196:
192:
188:
184:
180:
172:
168:
164:
160:
157:(also called
156:
147:
128:
122:
114:
107:
97:
86:
80:
70:
63:
55:
46:
33:
19:
2604:
2597:
2511:Vinyl halide
2468:
2398:Borinic acid
2393:Boronic acid
2370:Thioxanthate
2155:
1710:Hydrocarbons
1658:
1641:
1635:
1629:
1612:
1608:
1598:
1589:
1585:
1579:
1552:
1548:
1542:
1517:
1513:
1507:
1496:. Retrieved
1492:
1483:
1458:
1452:
1446:
1421:
1417:
1411:
1394:
1390:
1384:
1370:(20): 9101.
1367:
1363:
1357:
1340:
1336:
1330:
1316:: 44. 1964.
1313:
1309:
1300:
1281:
1277:
1267:
1230:
1226:
1216:
1197:
1191:
1166:
1160:
1151:
1134:
1130:
1120:
1111:
1086:
1080:
1046:
1042:
1036:
1019:
1015:
989:
983:
956:(1): 45–47.
953:
949:
923:
919:
888:(1): 54–56.
885:
881:
875:
848:
844:
821:
815:
801:isocyanamide
798:
791:
780:
777:Nomenclature
764:Xanthocillin
748:xanthocillin
741:
739:
715:
683:
654:
630:
623:
621:
618:
603:
595:Ugi reaction
584:
581:
577:O → RNHC(O)H
563:
560:
540:electrophile
535:
528:benzoxazoles
521:
503:allyl iodide
496:
484:
442:
437:
419:
399:
383:NH][ArSO
329:
321:
310:
308:
296:
285:
278:
272:
268:
258:
248:
245:
242:Spectroscopy
216:
209:
186:
177:. It is the
162:
158:
154:
152:
2640:Isocyanides
2575:Thiocyanate
2570:Sulfonamide
2535:Perchlorate
2523:Acyl halide
2484:Fluoroethyl
2365:Thionoester
2253:Phosphonium
2238:Phosphinate
2233:Phosphonous
2221:Phosphonate
1920:Hydroperoxy
1742:Cyclopropyl
1555:: 209–310.
1233:: 732–737.
822:isocyanides
542:such as an
445:-butylamine
428:to produce
402:formic acid
332:dehydration
231:double bond
227:triple bond
163:carbylamine
2634:Categories
2479:Haloalkane
2350:Thioketone
2305:Persulfide
2201:Phosphorus
2166:Isocyanate
2156:Isonitrile
2057:or oxygen
2055:hydrogen,
2051:not being
2032:Orthoester
1925:Dioxiranes
1903:Enol ether
1791:1-Propenyl
1592:: 219–227.
1498:2018-12-20
1397:(4): 284.
807:References
766:is a rare
752:antibiotic
566:formamides
426:chloroform
387:] + [C
352:diphosgene
336:formamides
251:relaxation
201:Properties
159:isonitrile
155:isocyanide
32:Isocyanate
18:Isonitrile
2612:inorganic
2446:Tellurium
2360:Thioester
2325:Sulfoxide
2310:Disulfide
2298:Sulfonium
2248:Phosphine
2226:Phosphite
2209:Phosphate
2141:Carbamate
2116:Hydrazone
2049:element,
2047:Only one
2020:Anhydride
1759:Methylene
1534:0002-7863
867:1463-9270
720:Fe(tBuNC)
610:carbonyls
557:Reactions
534:with the
449:catalytic
354:, or the
318:Synthesis
169:with the
146:resonance
108:¨
98:−
91:⟷
81:⊖
71:≡
64:⊕
56:−
2593:See also
2528:Chloride
2454:Tellurol
2408:Selenium
2375:Xanthate
2089:Ammonium
2071:Nitrogen
2053:carbon,
2010:Carboxyl
1977:Aldehyde
1965:Acryloyl
1947:carbonyl
1851:hydrogen
1806:Cumulene
1475:23443313
1438:21915395
1259:35821692
1103:16953613
1063:19408909
732:is not.
597:and the
524:oxazoles
367:Cl + 2 C
348:phosgene
305:Toxicity
255:coupling
217:Akin to
191:nitrogen
187:isocyano
165:) is an
144:General
2617:organic
2416:Selenol
2340:Sulfone
2293:Sulfide
2191:NONOate
2186:Nitroso
2176:Nitrite
2171:Nitrate
2161:Cyanate
2151:Nitrile
2136:Amidine
2131:Imidate
2101:Nitrene
2096:Hydrazo
2084:Enamine
2015:Acetoxy
2003:carboxy
1970:Benzoyl
1908:Epoxide
1891:Methoxy
1881:Alcohol
1835:Carbene
1769:Methine
1343:: 232.
1250:9235834
1171:Bibcode
890:Bibcode
698:(tBuNC)
573:RNC + H
420:In the
183:nitrile
2516:Iodide
2436:Selone
2280:Sulfur
1989:Ketone
1982:Ketene
1960:Acetyl
1915:Peroxy
1886:Alkoxy
1876:Acetal
1857:oxygen
1846:carbon
1830:Alkyne
1823:Benzyl
1818:Phenyl
1801:Allene
1796:Crotyl
1776:Alkene
1764:Bridge
1752:Pentyl
1737:Propyl
1727:Methyl
1567:
1532:
1473:
1436:
1257:
1247:
1137:: 75.
1101:
1061:
865:
783:prefix
727:Fe(CO)
692:forms
468:+ CHCl
434:amines
195:carbon
179:isomer
2548:Other
2385:Boron
2355:Thial
2288:Thiol
2181:Nitro
2146:Imide
2126:Amide
2111:Oxime
2106:Imine
2079:Amine
2027:Ester
1994:Ynone
1898:Ether
1869:R-O-R
1844:Only
1786:Allyl
1781:Vinyl
1747:Butyl
1732:Ethyl
1722:Alkyl
794:amine
499:allyl
395:NH]Cl
311:e.g.,
265:Odour
2470:Halo
1955:Acyl
1855:and
1813:Aryl
1613:1980
1590:1981
1565:ISBN
1530:ISSN
1471:PMID
1434:PMID
1255:PMID
1099:PMID
1059:PMID
863:ISSN
799:The
709:(CO)
526:and
505:and
443:tert
438:tert
2121:Azo
1646:doi
1617:doi
1557:doi
1522:doi
1518:109
1463:doi
1426:doi
1399:doi
1372:doi
1368:115
1345:doi
1318:doi
1286:doi
1245:PMC
1235:doi
1204:doi
1179:doi
1139:doi
1091:doi
1087:128
1051:doi
1024:doi
994:doi
990:112
958:doi
928:doi
898:doi
853:doi
464:CNH
334:of
276:sic
259:ca.
175:N≡C
161:or
153:An
2636::
1853:,
1848:,
1642:25
1640:.
1611:.
1588:.
1563:.
1553:22
1551:.
1528:.
1516:.
1491:.
1469:.
1459:42
1457:.
1432:.
1420:.
1395:21
1393:.
1366:.
1341:55
1339:.
1314:44
1312:.
1308:.
1282:23
1280:.
1276:.
1253:.
1243:.
1231:18
1229:.
1225:.
1177:.
1167:70
1165:.
1135:46
1133:.
1129:.
1097:.
1085:.
1071:^
1057:.
1047:74
1045:.
1018:.
1006:^
988:.
982:.
970:^
952:.
940:^
924:36
922:.
910:^
896:.
886:79
884:.
861:.
849:22
847:.
843:.
829:^
705:Fe
694:Fe
659:.
652:.
650:CN
646:CH
642:NC
638:CH
601:.
568::
546:.
509:.
460:Me
412:.
350:,
346:,
342:,
294:.
238:.
1694:e
1687:t
1680:v
1652:.
1648::
1623:.
1619::
1573:.
1559::
1536:.
1524::
1501:.
1477:.
1465::
1440:.
1428::
1422:9
1405:.
1401::
1378:.
1374::
1351:.
1347::
1324:.
1320::
1294:.
1288::
1261:.
1237::
1210:.
1206::
1185:.
1181::
1173::
1145:.
1141::
1105:.
1093::
1065:.
1053::
1030:.
1026::
1020:4
1000:.
996::
964:.
960::
954:6
934:.
930::
904:.
900::
892::
869:.
855::
729:5
722:5
716:t
711:9
707:2
700:9
696:2
648:3
640:3
634:a
631:K
627:a
624:K
575:2
480:O
478:2
474:3
470:3
466:2
462:3
393:5
391:H
389:5
385:3
381:5
379:H
377:5
373:5
371:H
369:5
365:2
173:–
129:]
123::
119:C
115:=
105:N
94:R
87::
78:C
61:N
52:R
47:[
34:.
20:)
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