118:
324:
31:
144:
343:. Some sultones are short-lived intermediates, used as strong alkylating agents to introduce a negatively charged sulfonate group. In the presence of water, they slowly hydrolyze to the hydroxy sulfonic acids. Sultone
354:
545:
495:
699:
719:
663:
286:
17:
312:
815:
766:
Beisler, J. A.; Sato, Y. (1971). "Chemistry of carpesterol, a novel sterol from
Solanum xanthocarpum".
820:
714:
R. J. Cremlyn “An
Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996)
121:
39:
661:
Adolf
Strecker (1868). "Ueber eine neue Bildungsweise und die Constitution der Sulfosäuren".
731:
Mondal, Shovan (2012). "Recent
Developments in the Synthesis and Application of Sultones".
470:
8:
825:
336:
307:
Sulfonates are commonly used to confer water solubility to protein crosslinkers such as
340:
148:
136:
109:, and colorless. Many useful compounds and even some biochemicals feature sulfonates.
791:
783:
748:
715:
695:
246:
An alternative is the condensation of a sulfonyl halide with an alcohol in pyridine:
191:
147:
Water-softening usually involves removal of calcium ions in water using a sulfonated
132:
775:
740:
672:
520:
202:
190:. Due to the stability of sulfonate anions, the cations of sulfonate salts such as
187:
71:
47:
292:
Sulfonic esters are used as reagents in organic synthesis, chiefly because the RSO
408:
301:
694:. Vol. A: Structure and Mechanisms (5th ed.). Springer. p. 414.
171:
117:
102:
809:
787:
676:
297:
90:
59:
285:
group and the R group is a trifluoromethyl group, the resulting compound is
752:
795:
278:
779:
348:
195:
129:
744:
30:
636:
323:
106:
143:
641:
579:
387:
366:
347:
are key intermediates in the synthesis of the anti-convulsant drug
125:
631:
213:
105:
of sulfonic acids. Sulfonates are generally stable in water, non-
98:
282:
221:
217:
210:
80:
76:
277:. Individual members of the category are named analogously to
433:
344:
155:
94:
55:
51:
183:
690:
Carey, Francis A.; Sundberg, Richard J. (2007).
27:
Organosulfur compound of the form R–S(=O)2–O (charge –1)
807:
304:, for example, is a strong methylating reagent.
759:
660:
689:
300:, especially when R is electron-withdrawing.
765:
322:
186:, the corresponding sulfonates are weak
142:
116:
29:
14:
808:
730:
311:-hydroxysulfosuccinimide (Sulfo-NHS),
279:how ordinary carboxyl esters are named
182:. As sulfonic acids tend to be strong
498:(closylate, chlorobenzenesulfonate),
170:are called sulfonates. They are the
552:-iodobenzenesulfonate derivative),
281:. For example, if the R group is a
269:Esters with the general formula RSO
24:
331:Cyclic sulfonic esters are called
264:
220:, typically in the presence of an
112:
25:
837:
768:The Journal of Organic Chemistry
664:Annalen der Chemie und Pharmacie
287:methyl trifluoromethanesulfonate
174:of sulfonic acids with formula
724:
708:
683:
654:
13:
1:
647:
390:(trifluoromethanesulfonate),
357:is an example of a sultone.
7:
625:
360:
318:
207:Strecker sulfite alkylation
10:
842:
692:Advanced Organic Chemistry
89:, where R is typically an
590:-nitrobenzenesulfonate),
158:with the general formula
101:atom. Sulfonates are the
677:10.1002/jlac.18681480108
523:(camsilate, camsylate),
124:are detergents found in
576:, where R is any group.
122:Alkylbenzene sulfonates
328:
152:
140:
40:organosulfur chemistry
35:
326:
205:of sulfonates is the
146:
120:
33:
440:-toluenesulfonate),
411:(esilate, esylate),
369:(methanesulfonate),
194:have application as
780:10.1021/jo00824a022
337:propane-1,3-sultone
335:. Two examples are
327:Propane-1,3-sultone
315:, Sulfo-SMCC, etc.
341:1,4-butane sultone
329:
153:
149:ion-exchange resin
141:
137:dishwashing liquid
36:
34:The sulfonate ion.
816:Functional groups
774:(25): 3946–3950.
745:10.1021/cr2003294
739:(10): 5339–5355.
701:978-0-387-44899-2
216:salt displaces a
192:scandium triflate
133:laundry detergent
70:, containing the
62:. Its formula is
16:(Redirected from
833:
800:
799:
763:
757:
756:
728:
722:
712:
706:
705:
687:
681:
680:
658:
621:
620:
619:
616:
575:
574:
573:
570:
542:
541:
540:
537:
521:Camphorsulfonate
517:
516:
515:
512:
492:
491:
490:
487:
471:Benzenesulfonate
467:
466:
465:
462:
430:
429:
428:
425:
405:
404:
403:
400:
384:
383:
382:
379:
296:group is a good
260:
242:
181:
169:
168:
167:
164:
88:
72:functional group
69:
21:
841:
840:
836:
835:
834:
832:
831:
830:
806:
805:
804:
803:
764:
760:
729:
725:
713:
709:
702:
688:
684:
659:
655:
650:
628:
617:
614:
613:
611:
607:
603:
599:
571:
568:
567:
565:
561:
557:
538:
535:
534:
532:
528:
524:
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510:
509:
507:
503:
499:
488:
485:
484:
482:
478:
474:
463:
460:
459:
457:
453:
449:
445:
426:
423:
422:
420:
416:
412:
409:Ethanesulfonate
401:
398:
397:
395:
391:
380:
377:
376:
374:
370:
363:
321:
302:Methyl triflate
295:
275:sulfonic esters
272:
267:
265:Sulfonic esters
258:
254:
250:
240:
236:
232:
228:
179:
175:
172:conjugate bases
165:
162:
161:
159:
115:
113:Sulfonate salts
103:conjugate bases
86:
74:
67:
63:
28:
23:
22:
18:Sulfonate ester
15:
12:
11:
5:
839:
829:
828:
823:
821:Leaving groups
818:
802:
801:
758:
723:
707:
700:
682:
652:
651:
649:
646:
645:
644:
639:
634:
627:
624:
623:
622:
609:
605:
601:
577:
563:
559:
543:
530:
526:
518:
505:
501:
493:
480:
476:
468:
455:
451:
447:
431:
418:
414:
406:
393:
385:
372:
362:
359:
320:
317:
293:
273:OR are called
270:
266:
263:
262:
261:
256:
252:
244:
243:
238:
234:
230:
209:, in which an
177:
114:
111:
84:
65:
26:
9:
6:
4:
3:
2:
838:
827:
824:
822:
819:
817:
814:
813:
811:
797:
793:
789:
785:
781:
777:
773:
769:
762:
754:
750:
746:
742:
738:
734:
727:
721:
720:0-471-95512-4
717:
711:
703:
697:
693:
686:
678:
674:
670:
666:
665:
657:
653:
643:
640:
638:
635:
633:
630:
629:
597:
593:
589:
585:
581:
578:
555:
551:
547:
544:
522:
519:
497:
494:
472:
469:
443:
439:
435:
432:
410:
407:
389:
386:
368:
365:
364:
358:
356:
352:
350:
346:
342:
338:
334:
325:
316:
314:
310:
305:
303:
299:
298:leaving group
290:
288:
284:
280:
276:
249:
248:
247:
227:
226:
225:
223:
219:
215:
212:
208:
204:
199:
197:
193:
189:
185:
173:
157:
150:
145:
138:
134:
131:
127:
123:
119:
110:
108:
104:
100:
96:
92:
91:organyl group
82:
78:
73:
61:
60:sulfonic acid
57:
53:
49:
45:
41:
32:
19:
771:
767:
761:
736:
732:
726:
710:
691:
685:
671:(1): 90–96.
668:
662:
656:
595:
591:
587:
583:
553:
549:
473:(besylate),
441:
437:
353:
332:
330:
308:
306:
291:
274:
268:
245:
206:
200:
154:
43:
37:
355:Tisocromide
255:Cl → ROSO
224:catalyst:
203:preparation
196:Lewis acids
97:group or a
826:Sulfonates
810:Categories
648:References
349:zonisamide
251:ROH + R'SO
201:A classic
130:toothpaste
788:0022-3263
733:Chem. Rev
637:Sulfoxide
546:Pipsylate
496:Closilate
107:oxidizing
44:sulfonate
753:22742473
642:Sulfonyl
626:See also
580:Nosylate
434:Tosylate
388:Triflate
367:Mesylate
361:Examples
333:sultones
319:Sultones
259:R' + HCl
126:shampoos
796:5127991
632:Sulfate
214:sulfite
176:R−S(=O)
99:halogen
64:R−S(=O)
794:
786:
751:
718:
698:
345:oximes
283:methyl
241:M + MX
237:→ RSO
229:RX + M
222:iodine
218:halide
211:alkali
156:Anions
139:, etc.
594:- or
586:- or
533:O)−SO
188:bases
184:acids
95:amino
58:of a
56:ester
52:anion
46:is a
792:PMID
784:ISSN
749:PMID
716:ISBN
696:ISBN
500:Cl−C
339:and
160:R−SO
48:salt
42:, a
776:doi
741:doi
737:112
673:doi
669:148
612:−SO
604:N−C
566:−SO
558:I−C
508:−SO
483:−SO
458:−SO
421:−SO
396:−SO
375:−SO
313:BS3
180:−OH
54:or
38:In
812::
790:.
782:.
772:36
770:.
747:.
735:.
667:.
531:15
527:10
525:(C
450:−C
446:CH
417:CH
413:CH
392:CF
371:CH
351:.
289:.
233:SO
198:.
135:,
128:,
93:,
87:−O
79:(=
68:−O
50:,
798:.
778::
755:.
743::
704:.
679:.
675::
618:3
615:−
610:4
608:H
606:6
602:2
600:O
598:-
596:p
592:o
588:p
584:o
582:(
572:3
569:−
564:4
562:R
560:6
556:-
554:p
550:p
548:(
539:3
536:−
529:H
514:3
511:−
506:4
504:H
502:6
489:3
486:−
481:5
479:H
477:6
475:C
464:3
461:−
456:4
454:H
452:6
448:3
444:-
442:p
438:p
436:(
427:3
424:−
419:2
415:3
402:3
399:−
394:3
381:3
378:−
373:3
309:N
294:3
271:2
257:2
253:2
239:3
235:3
231:2
178:2
166:3
163:−
151:.
85:2
83:)
81:O
77:S
75:−
66:2
20:)
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