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Nitrilium

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Nitriles are only weakly basic and are poor nucleophiles, but they will attack very reactive electrophiles such as
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Nitrilium ions are believed to be intermediates in the hydrolysis of nitriles, the
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Nitrilium salts can be prepared by reacting nitriles with
337:(6th ed.). New York: John Wiley & Sons. p.  301:(6th ed.). New York: John Wiley & Sons. p.  229:(6th ed.). New York: John Wiley & Sons. p.  269:(1st ed.). Oxford University Press. p. 294. 197:(1st ed.). Oxford University Press. p. 436. 161:(1st ed.). Oxford University Press. p. 200. 417: 325: 289: 217: 400: 407: 393: 20:The general structures of nitrilium ions 15: 418: 139: 359: 74: 13: 14: 442: 363: 319: 283: 247: 211: 175: 124: 1: 117: 379:. You can help Knowledge by 43: 7: 10: 447: 358: 333:Advanced Organic Chemistry 297:Advanced Organic Chemistry 225:Advanced Organic Chemistry 426:Organic compound stubs 371:This article about an 98:with ketones, and the 81:Beckmann rearrangement 21: 57:trialkyloxonium salts 19: 329:; Smith, M. (2007). 293:; Smith, M. (2007). 221:; Smith, M. (2007). 61:sodium borohydride 22: 388: 387: 348:978-0-471-72091-1 312:978-0-471-72091-1 276:978-0-19-850346-0 267:Organic Chemistry 257:; Greeves, Nick; 255:Clayden, Jonathan 240:978-0-471-72091-1 204:978-0-19-850346-0 195:Organic Chemistry 185:; Greeves, Nick; 183:Clayden, Jonathan 168:978-0-19-850346-0 159:Organic Chemistry 149:; Greeves, Nick; 147:Clayden, Jonathan 438: 409: 402: 395: 373:organic compound 367: 360: 353: 352: 336: 323: 317: 316: 300: 287: 281: 280: 251: 245: 244: 228: 215: 209: 208: 179: 173: 172: 143: 137: 128: 96:Schmidt reaction 75:As intermediates 446: 445: 441: 440: 439: 437: 436: 435: 416: 415: 414: 413: 357: 356: 349: 324: 320: 313: 288: 284: 277: 252: 248: 241: 216: 212: 205: 180: 176: 169: 144: 140: 131:IUPAC Gold Book 129: 125: 120: 77: 70: 46: 12: 11: 5: 444: 434: 433: 428: 412: 411: 404: 397: 389: 386: 385: 368: 355: 354: 347: 318: 311: 282: 275: 263:Wothers, Peter 259:Warren, Stuart 246: 239: 210: 203: 191:Wothers, Peter 187:Warren, Stuart 174: 167: 155:Wothers, Peter 151:Warren, Stuart 138: 135:nitrilium ions 122: 121: 119: 116: 85:Friedel-Crafts 76: 73: 68: 45: 42: 32:that has been 9: 6: 4: 3: 2: 443: 432: 429: 427: 424: 423: 421: 410: 405: 403: 398: 396: 391: 390: 384: 382: 378: 374: 369: 366: 362: 361: 350: 344: 340: 335: 334: 328: 322: 314: 308: 304: 299: 298: 292: 286: 278: 272: 268: 264: 260: 256: 250: 242: 236: 232: 227: 226: 220: 214: 206: 200: 196: 192: 188: 184: 178: 170: 164: 160: 156: 152: 148: 142: 136: 132: 127: 123: 115: 113: 109: 105: 101: 97: 93: 92:isoquinolines 90:of amines to 89: 86: 82: 72: 66: 62: 58: 53: 51: 41: 39: 35: 31: 27: 18: 381:expanding it 370: 332: 321: 296: 285: 266: 249: 224: 213: 194: 177: 158: 141: 126: 78: 54: 50:carbocations 47: 25: 23: 114:reactions. 88:cyclization 420:Categories 118:References 34:protonated 327:March, J. 291:March, J. 219:March, J. 112:Passerini 44:Synthesis 38:alkylated 28:ion is a 26:nitrilium 431:Nitriles 265:(2001). 193:(2001). 157:(2001). 71:—NH—R′. 65:diglyme 36:, , or 30:nitrile 345:  309:  273:  237:  201:  165:  108:Pinner 104:Ritter 94:, the 83:, the 375:is a 377:stub 343:ISBN 339:1613 307:ISBN 271:ISBN 235:ISBN 231:1814 199:ISBN 163:ISBN 110:and 40:, . 303:716 100:Ugi 63:in 422:: 341:. 305:. 261:; 233:. 189:; 153:; 133:: 106:, 102:, 52:. 24:A 408:e 401:t 394:v 383:. 351:. 315:. 279:. 243:. 207:. 171:. 69:2

Index


nitrile
protonated
alkylated
carbocations
trialkyloxonium salts
sodium borohydride
diglyme
Beckmann rearrangement
Friedel-Crafts
cyclization
isoquinolines
Schmidt reaction
Ugi
Ritter
Pinner
Passerini
IUPAC Gold Book
nitrilium ions
Clayden, Jonathan
Warren, Stuart
Wothers, Peter
ISBN
978-0-19-850346-0
Clayden, Jonathan
Warren, Stuart
Wothers, Peter
ISBN
978-0-19-850346-0
March, J.

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