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Rosenmund–von Braun reaction

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improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction. Further improvement of the reaction was done in the following years, for example the use of
134:, not the nitrile, but Rosenmund speculated that the intermediate should be the nitrile, since nitriles on aromatic rings can react to form carboxylic acids. Independently 139: 135: 207:"Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe" 70: 355:
Wu, Jeff Xin; Beck, Brandon; Ren, Rex X. (January 2002). "Catalytic Rosenmund–von Braun reaction in halide-based ionic liquids".
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who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of
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KOELSCH, C. F.; WHITNEY, A. G. (November 1941). "THE ROSENMUND-von BRAUN NITRILE SYNTHESIS".
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v. Braun, Julius; Manz, Gottfried (1931). "Fluoranthen und seine Derivate. III. Mitteilung".
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E. Callen, Joseph; A. Dornfeld, Clinton; H. Coleman, George (1948). "9-CYANOPHENANTHRENE".
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Pongratz, Alfred (July 1927). "Untersuchungen über Perylen und seine Derivate".
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Berichte der Deutschen Chemischen Gesellschaft (A and B Series)
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Rosenmund, Karl W.; Struck, Erich (27 September 1919).
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a similar reaction for the synthesis of alkyl nitrile
380: 204: 327: 238: 354: 292: 156: 130:at 200 °C. The reaction yields the 286: 234: 232: 381: 321: 200: 198: 229: 195: 13: 241:Justus Liebig's Annalen der Chemie 14: 405: 348: 330:The Journal of Organic Chemistry 110: 259: 1: 369:10.1016/S0040-4039(01)02168-2 188: 154:as solvent for the reaction. 118:The reaction was named after 85:Rosenmund–von Braun synthesis 19:Rosenmund-von Braun reaction 56:rosenmund-von-braun-reaction 7: 165: 10: 410: 126:and catalytic amounts of 77: 51:Organic Chemistry Portal 45: 18: 280:10.15227/orgsyn.028.0034 253:10.1002/jlac.19314880107 223:10.1002/cber.19190520840 172:Kolbe nitrile synthesis 389:Substitution reactions 295:Monatshefte für Chemie 162: 120:Karl Wilhelm Rosenmund 28:Karl Wilhelm Rosenmund 160: 40:Substitution reaction 357:Tetrahedron Letters 342:10.1021/jo01206a002 307:10.1007/BF01518076 183:Von Braun reaction 178:Sandmeyer reaction 163: 268:Organic Syntheses 124:potassium cyanide 81: 80: 31:Julius von Braun 401: 373: 372: 352: 346: 345: 325: 319: 318: 290: 284: 283: 263: 257: 256: 236: 227: 226: 217:(8): 1749–1756. 202: 148: 140:Julius von Braun 114: 89:organic reaction 73: 58: 16: 15: 409: 408: 404: 403: 402: 400: 399: 398: 379: 378: 377: 376: 353: 349: 326: 322: 291: 287: 264: 260: 237: 230: 203: 196: 191: 168: 142: 136:Alfred Pongratz 132:carboxylic acid 128:cuprous cyanide 97:cuprous cyanide 69: 54: 30: 12: 11: 5: 407: 397: 396: 394:Name reactions 391: 375: 374: 363:(3): 387–389. 347: 336:(6): 795–803. 320: 301:(7): 585–591. 285: 258: 247:(1): 111–126. 228: 193: 192: 190: 187: 186: 185: 180: 175: 167: 164: 116: 115: 79: 78: 75: 74: 67: 60: 59: 52: 48: 47: 43: 42: 37: 36:Reaction type 33: 32: 25: 21: 20: 9: 6: 4: 3: 2: 406: 395: 392: 390: 387: 386: 384: 370: 366: 362: 358: 351: 343: 339: 335: 331: 324: 316: 312: 308: 304: 300: 296: 289: 281: 277: 273: 269: 262: 254: 250: 246: 242: 235: 233: 224: 220: 216: 212: 208: 201: 199: 194: 184: 181: 179: 176: 173: 170: 169: 161:Other example 159: 155: 153: 152:ionic liquids 146: 141: 137: 133: 129: 125: 121: 113: 109: 108: 107: 105: 102: 98: 94: 90: 86: 76: 72: 68: 65: 62: 61: 57: 53: 50: 49: 44: 41: 38: 35: 34: 29: 26: 23: 22: 17: 360: 356: 350: 333: 329: 323: 298: 294: 288: 271: 267: 261: 244: 240: 214: 210: 117: 99:to yield an 95:reacts with 91:in which an 84: 82: 71:RXNO:0000288 66:ontology ID 46:Identifiers 24:Named after 143: [ 93:aryl halide 383:Categories 274:(28): 34. 189:References 315:197767053 166:See also 104:nitrile 313:  87:is an 311:S2CID 147:] 138:and 101:aryl 83:The 365:doi 338:doi 303:doi 276:doi 249:doi 245:488 219:doi 64:RSC 385:: 361:43 359:. 334:06 332:. 309:. 299:48 297:. 272:28 270:. 243:. 231:^ 215:52 213:. 209:. 197:^ 145:de 106:. 371:. 367:: 344:. 340:: 317:. 305:: 282:. 278:: 255:. 251:: 225:. 221::

Index

Karl Wilhelm Rosenmund
Substitution reaction
rosenmund-von-braun-reaction
RSC
RXNO:0000288
organic reaction
aryl halide
cuprous cyanide
aryl
nitrile
Rosenmund–von Braun synthesis
Karl Wilhelm Rosenmund
potassium cyanide
cuprous cyanide
carboxylic acid
Alfred Pongratz
Julius von Braun
de
ionic liquids

Kolbe nitrile synthesis
Sandmeyer reaction
Von Braun reaction


"Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe"
doi
10.1002/cber.19190520840

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