20:
280:
187:
533:
332:. However, the observed moment is only 4.7 D, suggesting a substantial resonance contribution in which the other nitrogen bears negative charge (–N–N(=O)–).
738:
344:
transazobenzene compounds isomerize to their cis isomers, analogous to azobenzene. Similar reaction conditions can instead cause isomery to an
125:
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613:
436:
707:
329:
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64:
767:
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363:. Correspondingly, the reaction is possible under UV light with wavelength approximately 220 nm.
237:
645:
367:
314:
100:
515:
491:
303:
O, the N-N and N-O bond lengths are is 1.24 and 1.255 Å respectively, corresponding to some
677:. The Chemistry of Functional Groups. Vol. 1. Chichester, UK: John Wiley & Sons, Ltd.
600:. The Chemistry of Functional Groups. Vol. 1. Chichester, UK: John Wiley & Sons, Ltd.
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with arsenous oxide. Such reactions are proposed to proceed via the intermediacy of the
475:
416:
Azoxy compounds are weak bases, and unstable to strong acids. Azoxyarenes undergo the
360:
318:
104:
96:
84:
751:
714:
455:
406:
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326:
322:
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decarboxylate in strong base to an azotate susceptible to strong alkylation agents:
503:
352:
292:
88:
56:
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268:
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24:
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hydrogens must be situated between two azoxy groups to appreciably dissociate.
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264:
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672:
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542:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
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429:
279:
32:
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222:
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H. E. Bigelow and Albert Palmer "Azoybenzene" Org. Synth. 1931, 11, 16.
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differently. In the case of azoxybenzene, PhNN(O)– reacts at the
391:
92:
348:-azophenol, or migration of the oxygen atom across the two nitrogens.
371:
108:
278:
192:
80:
18:
494:
preserves the azoxy group even as it reduces arene substituents.
68:
632:
González Martínez, Sandra
Patricia; Bernès, Sylvain (2007). "
325:
on oxygen (–N=N(O)–) corresponds to a theoretical 6‑
182:{\displaystyle {\ce {PhNHOH + PhNO -> PhN(O)NPh + H2O}}}
79:
Azoxybenzene and its derivatives are typically prepared by
638:
23:
The structure of the azoxy functional group, where R is a
172:
409:
eliminate the leaving group to give an indazolone (the
382:–N(O)=NC(H)< + 2LiR → –N=NC(R)< + Li
128:
355:, azoxy compounds do not fragment thermally to lose
462:give a deep-blue radical anion, which dimerizes in
598:The Chemistry of the Hydrazo, Azo and Azoxy Groups
454:Electrochemical reduction converts azoxyarenes to
424:-azophenols; primary and secondary azoxyaliphates
181:
705:Guideline On The Limits Of Genotoxic Impurities
291:Azoxybenzene compounds are more stable as their
443:position, while PhN(O)N– reacts at the
8:
435:The two aryl groups in azoxyarenes undergo
378:replace the hydrogens, but with reduction:
283:Structure of azoxybenzene as determined by
263:An alternative route involves oxidation of
490:selects out the azoxy link. Conversely,
171:
166:
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129:
127:
16:Chemical compound of the form R–N=N(–O)–R
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587:
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370:, but in non-oxidizing media, aliphatic
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67:. Most azoxy-containing compounds have
737:: CS1 maint: archived copy as title (
730:
466:to the corresponding azo compound and
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625:
7:
307:. The CNNC and CNNO are near 176°.
437:electrophilic aromatic substitution
539:Compendium of Chemical Terminology
470:. Strong reducing agents such as
14:
674:Double-Bonded Functional Groups
671:Patai, Saul, ed. (1977-03-16).
596:Patai, Saul, ed. (1975-01-01).
506:are suspected to be genotoxic.
405:to a benzylic carbon with good
361:forbidden by orbital symmetries
152:
146:
139:
1:
502:Alkyl azoxy compounds, e.g.
398:, leading to dimerization.
87:, such as the reduction of
47:with the general structure
784:
460:Single-electron reductants
394:abstract α hydrogens in a
359:; the process is believed
658:10.1107/S1600536807035787
636:-Diphenyldiazene Oxide".
568:10.15227/orgsyn.011.0016
486:arene substituents, but
472:lithium aluminum hydride
65:cycloadd to double bonds
552:10.1351/goldbook.A00567
488:catalytic hydrogenation
305:double bonds character
288:
183:
59:. Azoxy compounds are
51:. They are considered
28:
683:10.1002/9780470771501
418:Wallach rearrangement
411:Davis-Beirut reaction
285:X-ray crystallography
282:
184:
22:
396:free-radical process
368:electron-withdrawing
252:→ –N(N=O)R + R
126:
650:2007AcCrE..63O3639G
366:The azoxy group is
225:→ –N=NOK + CO
174:
101:phenylhydroxylamine
606:10.1002/0470023414
516:azobenzene dioxide
492:sodium borohydride
289:
179:
162:
29:
758:Functional groups
692:978-0-470-77150-1
615:978-0-471-66924-1
468:hydrogen peroxide
342:ultraviolet light
210:→ –N(N=O)CO
191:Nitrosocarbamate
177:
165:
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43:sharing a common
41:organic compounds
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713:. Archived from
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478:electronegative
464:aqueous solution
321:with a negative
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45:functional group
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768:Azoxy compounds
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708:"Archived copy"
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544:azoxy compounds
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236:–N=NOK +
232:
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217:–N(N=O)CO
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39:are a group of
37:azoxy compounds
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319:resonance form
315:azoxydibenzene
300:
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105:nitrosobenzene
97:hydroxylamines
95:compounds and
85:nitrocompounds
76:
73:
71:substituents.
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6:
4:
3:
2:
780:
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763:Azo compounds
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720:on 2006-09-04
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476:hydrogenolyze
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456:azo compounds
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407:leaving group
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357:nitrous oxide
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330:dipole moment
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323:formal charge
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295:isomer. In Ph
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199:–N(H)CO
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57:azo compounds
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722:. Retrieved
715:the original
701:
673:
666:
644:(8): o3639.
641:
637:
633:
597:
558:
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529:
504:azoxymethane
501:
483:
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453:
448:
444:
440:
434:
421:
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402:
401:Azoxyarenes
400:
389:
365:
350:
345:
339:
310:
309:
293:trans isomer
290:
269:peroxy acids
262:
190:
89:nitrobenzene
78:
36:
30:
451:positions.
430:hydrazamide
426:tautomerize
376:Alkyllithia
265:azobenzenes
75:Preparation
61:1,3-dipoles
49:R−N=N(−O)−R
25:substituent
752:Categories
724:2007-07-11
522:References
336:Reactions
275:Structure
140:⟶
81:reduction
33:chemistry
733:cite web
510:See also
392:oxidants
214:R + HNO3
53:N-oxides
646:Bibcode
386:O↓ + RH
351:Unlike
256:O + KBF
99:, e.g.
93:nitroso
689:
612:
498:Safety
390:Basic
340:Under
193:esters
131:PhNHOH
109:phenyl
107:(Ph =
718:(PDF)
711:(PDF)
634:trans
534:IUPAC
480:ortho
474:also
445:ortho
428:to a
403:ortho
346:ortho
311:Trans
267:with
221:R + K
203:R + 2
739:link
687:ISBN
610:ISBN
484:para
449:para
447:and
441:meta
422:para
137:PhNO
103:and
69:aryl
63:and
679:doi
654:doi
602:doi
564:doi
548:doi
546:".
482:or
420:to
413:).
317:'s
242:OBF
229:+ R
157:NPh
143:PhN
122:):
83:of
55:of
31:In
754::
735:}}
731:{{
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652:.
642:63
640:.
624:^
608:.
574:^
536:,
458:.
432:.
271:.
223:OR
205:NO
111:,
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741:)
727:.
695:.
681::
660:.
656::
648::
618:.
604::
566::
550::
384:2
372:α
327:D
313:-
301:2
299:N
297:2
287:.
258:4
254:2
247:4
240:3
238:R
233:O
231:2
227:2
219:2
212:2
207:2
201:2
176:O
168:2
164:H
160:+
153:)
150:O
147:(
134:+
119:5
117:H
115:6
113:C
27:.
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