365:
17:
406:
346:
310:
274:
238:
202:
166:
399:
48:
Nitriles are only weakly basic and are poor nucleophiles, but they will attack very reactive electrophiles such as
425:
392:
84:
338:
230:
302:
80:
330:
294:
222:
8:
331:
295:
223:
111:
60:
430:
342:
306:
270:
234:
198:
162:
380:
372:
254:
182:
146:
95:
79:
Nitrilium ions are believed to be intermediates in the hydrolysis of nitriles, the
130:
107:
103:
376:
59:. The nitrilium ions thus formed can then be reduced to secondary amines with
419:
262:
258:
190:
186:
154:
150:
91:
99:
326:
290:
218:
87:
56:
49:
134:
33:
37:
16:
364:
64:
29:
67:. This is a convenient route to secondary amines of the form RCH
253:
181:
145:
55:
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
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.