265:
24:
298:-Bu)", which decomposes at 60 °C to give the diimide. A second route to sulfur diimides involve treatment of sulfur tetrafluoride with amines. A third route involves transimidation of disulfonylsulfodiimide:
156:
475:
Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167.
454:
131:
583:
225:
588:
256:, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful reagents.
379:
492:
Kresze, GĂĽnter; Braxmeier, Hans; MĂĽnsterer, Heribert (1987). "Allylcarbamates by the Aza-Ene
Reaction: Methyl
523:
Lork, Enno; Mews, Ruëdiger; Shakirov, Makhmut M.; Watson, Paul G.; Zibarev, Andrey V. (2002). "The first
387:
36:
360:. They have planar C–N=S=N–C cores with bent C–N=S and N=S=N geometries, and various combinations of
449:
291:
361:
562:
540:
505:
476:
345:
179:
92:
72:
284:
249:
219:
566:
544:
577:
375:
443:
117:
407:
561:: reactivity and coordination behavior", Coord. Chem. Rev. 1998, 176, 431-450.
277:
204:
83:
509:
23:
480:
557:
Fleischer, R.; Stalke, D., "A new route to sulfur polyimido anions S(NR)
403:
104:
264:
218:
Except where otherwise noted, data are given for materials in their
383:
245:
71:
61:
390:
attack at the sulfur to give the corresponding nitrogen anion:
406:
can be generated by treating the sulfur diimides with a
283:sulfurdiimide. It is prepared by reaction of
116:
8:
240:are chemical compounds of the formula S(NR)
91:
15:
471:
469:
336:-Bis(methoxycarbonyl)sulfur diimide (MeO
263:
465:
276:A particularly stable derivative is di-
161:
136:
531:′-polyfluorohetaryl sulfur diimide".
143:Key: HQFYRKYAKZRZCJ-UHFFFAOYSA-N
7:
371:are observed for the two N=S bonds.
107:
14:
496:-(2-Methyl-2-Butenyl)Carbamate".
455:Bis(trimethylsilyl)sulfur diimide
356:These compounds are related to SO
191:
185:
22:
244:. Structurally, they are the di
222:(at 25 °C , 100 kPa).
294:to give the intermediate "S(N-
197:
1:
567:10.1016/S0010-8545(98)00130-1
545:10.1016/S0022-1139(02)00047-7
533:Journal of Fluorine Chemistry
352:Structure, bonding, reactions
140:InChI=1S/H2N2S/c1-3-2/h1-2H
605:
402:The triimido analogues of
252:. The parent member, S(NH)
416:4 LiNHBu-t + 2 S(NBu-t)
216:
172:
152:
127:
53:
45:
35:
30:
21:
510:10.15227/orgsyn.065.0159
481:10.1002/anie.196701491
388:Organolithium reagents
273:
48:2λ-Diazathia-1,2-diene
446:- the carbon analogue
380:Diels–Alder reactions
344:Me) is obtained from
268:Structure of S(NBu-t)
267:
584:Sulfur(IV) compounds
374:Sulfur diimides are
260:Organic derivatives
212: g·mol
18:
450:Disulfur dinitride
274:
226:Infobox references
16:
589:Functional groups
498:Organic Syntheses
398:→ R'S(NR)(NRLi)
292:sulfur dichloride
234:Chemical compound
232:
231:
73:Interactive image
40:diimino-λ-sulfane
596:
569:
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548:
520:
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513:
489:
483:
473:
378:. They undergo
346:methyl carbamate
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180:Chemical formula
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109:
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75:
26:
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238:Sulfur diimides
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65:
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17:Sulfur diimide
12:
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5:
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539:(2): 165–168.
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395:
394:R'Li + S(NR)
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337:
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250:sulfur dioxide
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220:standard state
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376:electrophilic
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444:Carbodiimide
401:
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328:
295:
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275:
237:
236:
54:Identifiers
46:Other names
428:+ 2 t-BuNH
408:metal amide
288:-butylamine
173:Properties
578:Categories
461:References
340:C-N=S=N-CO
205:Molar mass
84:ChemSpider
60:3D model (
37:IUPAC name
318:+ 2 PhSO
314:→ S(NR)
438:See also
424:S(NBu-t)
420:→ 2 Li
310:+ 2 RNH
527:-alkyl-
504:: 159.
404:sulfite
369:isomers
105:PubChem
384:dienes
281:-butyl
157:SMILES
118:336934
93:298618
31:Names
382:with
302:S(NSO
290:with
246:imine
210:62.09
164:N=S=N
132:InChI
62:JSmol
365:and
286:tert
563:doi
541:doi
537:115
506:doi
477:doi
306:Ph)
248:of
108:CID
580::
535:.
502:65
500:.
468:^
410::
386:.
348:.
334:N'
322:NH
565::
559:n
547:.
543::
529:N
525:N
512:.
508::
494:N
479::
430:2
426:3
422:2
418:2
396:2
367:Z
363:E
358:2
342:2
338:2
332:,
330:N
324:2
320:2
316:2
312:2
308:2
304:2
296:t
279:t
272:.
270:2
254:2
242:2
198:S
195:2
192:N
189:2
186:H
64:)
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