203:
657:
406:
24:
935:
Swenton, J. S.; Anderson, D. K.; Jackson, D. K.; Narasimhan, L. (1981). "1,4-Dipole-metalated quinone strategy to (±)-4-demethoxydaunomycinone and (±)-daunomycinone. Annelation of benzocyclobutenedione monoketals with lithioquinone bisketals".
419:
964:
Isibashi, H.; Okada, M.; Komatsu, H.; Ikeda, M. S. (1985). "A New
Synthesis of Substituted Cyclopentenones by Olefin Cyclization Initiated by Pummerer Reaction Intermediates".
907:
Ibarra, C. A; Rodgríguez, R. C; Monreal, M. C. F; Navarro, F. J. G.; Tesoreo, J. M. (1989). "One-pot synthesis of β-keto sulfones and β-keto sulfoxides from carboxylic acids".
791:
Kaiser, E. M.; Beard, R. D.; Hauser, C. R. (1973). "Preparation and reactions of the mono- and dialkali salts of dimethyl sulfone, dimethyl sulfoxide, and related compounds".
893:
769:
259:
1005:
1044:
656:
877:
217:
1049:
581:
384:
351:
426:
1012:
160:
181:
677:
96:
833:
Romo, D.; Myers, A. I. (1992). "An asymmetric route to enantiomerically pure 1,2,3-trisubstituted cyclopropanes".
585:
636:
1016:
763:
732:
Mukulesh Mondal "Sodium methylsulfinylmethylide: A versatile reagent" Synlett 2005, vol. 17, 2697-2698.
597:
628:
36:
198:
966:
793:
62:
983:
887:
496:
454:
388:
337:
873:
755:
707:
694:
613:
473:
458:
124:
975:
946:
917:
843:
801:
733:
715:
566:
462:
366:
320:
282:
169:
72:
202:
869:
861:
488:
450:
397:
805:
1038:
938:
909:
835:
149:
987:
492:
750:
640:
466:
23:
570:
331:
301:
115:
737:
979:
644:
612:), which can be useful intermediates. Reduction of β-ketosulfoxides with
950:
921:
847:
719:
136:
620:
617:
574:
479:, a number of additional uses for this reagent have been identified.
1027:
819:
396:
Except where otherwise noted, data are given for materials in their
601:
577:
95:
85:
580:. NaDMSO in DMSO is especially convenient in the generation of
186:
414:
697:; Chaykovsky, M. (1965). "Methylsulfinyl Carbanion (CH
487:
Sodium methylsulfinylmethylide is prepared by heating
705:). Formation and Applications to Organic Synthesis".
565:of DMSO is 35, which leads NaDMSO to be a powerful
1006:"The Dimethyl Sulfoxide (DMSO) Anion — Dimsyl Ion"
148:
866:Sulfur Ylides: Emerging Synthetic Intermediates
71:
678:"Sodium Hydride in Aprotic Solvents: Look Out"
369:, May be explosive in certain circumstances.
236:InChI=1S/C2H5OS.Na/c1-4(2)3;/h1H2,2H3;/q-1;+1
226:InChI=1S/C2H5OS.Na/c1-4(2)3;/h1H2,2H3;/q-1;+1
8:
892:: CS1 maint: multiple names: authors list (
768:: CS1 maint: multiple names: authors list (
635:). β-ketosulfoxides can also be used in the
689:
687:
627:). Reaction with alkyl halides followed by
201:
123:
15:
168:
669:
472:Since the first publication in 1965 by
314:White solid, solution in DMSO is green
264:
222:
197:
50:sodium dimsylate, dimsylsodium, NaDMSYL
885:
761:
569:. NaDMSO is used in the generation of
457:. This unusual salt has some uses in
246:Key: CWXOAQXKPAENDI-UHFFFAOYSA-N
229:Key: CWXOAQXKPAENDI-UHFFFAOYSA-N
7:
239:Key: CWXOAQXKPAENDI-UHFFFAOYAA
139:
14:
41:Sodium (methanesulfinyl)methanide
655:
404:
340:and many polar organic solvents
22:
631:gives α,β-unsaturated ketones (
400:(at 25 °C , 100 kPa).
17:Sodium methylsulfinylmethylide
1045:Reagents for organic chemistry
1028:"Preparation of dimsyl sodium"
1015:. October 2007. Archived from
820:"Preparation of dimsyl sodium"
582:dimethyloxosulfonium methylide
439:Sodium methylsulfinylmethylide
385:Dimethyloxosulfonium methylide
352:Occupational safety and health
1:
864:; Melvin, L. S., Jr. (1975).
806:10.1016/S0022-328X(00)95020-4
1013:Gaylord Chemical Corporation
751:"2,3-Diphenyl-1,3-Butadiene"
608:) to form β-ketosulfoxides (
449:) is the sodium salt of the
586:dimethylsulfonium methylide
1066:
779:, vol. 6, p. 531
749:Iwai, I.; Ide, J. (1988).
394:
373:
349:
344:
275:
255:
213:
55:
47:
35:
30:
21:
1050:Organosodium compounds
637:Pummerer rearrangement
738:10.1055/s-2005-917075
980:10.1055/s-1985-31290
592:Reaction with esters
306:100.13
37:Preferred IUPAC name
951:10.1021/jo00337a002
922:10.1021/jo00284a043
848:10.1021/jo00049a038
794:J. Organomet. Chem.
720:10.1021/ja01084a033
365:May form corrosive
321:Solubility in water
18:
455:dimethyl sulfoxide
427:Infobox references
389:dimethyl sulfoxide
374:Related compounds
16:
945:(24): 4825–4836.
916:(23): 5620–5623.
842:(23): 6265–6270.
777:Collected Volumes
756:Organic Syntheses
708:J. Am. Chem. Soc.
614:aluminium amalgam
459:organic chemistry
435:Chemical compound
433:
432:
380:Related compounds
182:CompTox Dashboard
97:Interactive image
1057:
1031:
1023:
1021:
1010:
992:
991:
974:(6/7): 643–645.
961:
955:
954:
932:
926:
925:
904:
898:
897:
891:
883:
858:
852:
851:
830:
824:
823:
816:
810:
809:
788:
782:
780:
773:
767:
759:
746:
740:
730:
724:
723:
714:(6): 1345–1353.
691:
682:
681:
674:
659:
417:
411:
408:
407:
336:Very soluble in
283:Chemical formula
206:
205:
190:
188:
172:
152:
141:
127:
99:
75:
26:
19:
1065:
1064:
1060:
1059:
1058:
1056:
1055:
1054:
1035:
1034:
1026:
1019:
1008:
1004:
1001:
996:
995:
963:
962:
958:
934:
933:
929:
906:
905:
901:
884:
880:
860:
859:
855:
832:
831:
827:
818:
817:
813:
790:
789:
785:
775:
760:
748:
747:
743:
731:
727:
704:
700:
693:
692:
685:
676:
675:
671:
666:
594:
564:
559:
554:
547:
543:
539:
535:
531:
527:
521:
517:
513:
509:
505:
485:
436:
429:
424:
423:
422: ?)
413:
409:
405:
401:
381:
362:
323:
295:
291:
285:
271:
268:
263:
262:
251:
248:
247:
241:
240:
237:
231:
230:
227:
221:
220:
209:
191:
184:
175:
155:
142:
130:
102:
89:
78:
65:
51:
43:
42:
12:
11:
5:
1063:
1061:
1053:
1052:
1047:
1037:
1036:
1033:
1032:
1024:
1022:on 2011-07-11.
1000:
999:External links
997:
994:
993:
956:
927:
899:
878:
870:Academic Press
853:
825:
811:
783:
741:
725:
702:
698:
683:
668:
667:
665:
662:
661:
660:
593:
590:
562:
558:
555:
553:
550:
549:
548:
545:
541:
537:
533:
529:
525:
522:
519:
515:
511:
507:
503:
489:sodium hydride
484:
481:
451:conjugate base
434:
431:
430:
425:
403:
402:
398:standard state
395:
392:
391:
382:
379:
376:
375:
371:
370:
363:
360:
357:
356:
347:
346:
342:
341:
334:
328:
327:
324:
319:
316:
315:
312:
308:
307:
304:
298:
297:
293:
289:
286:
281:
278:
277:
273:
272:
270:
269:
266:
258:
257:
256:
253:
252:
250:
249:
245:
244:
242:
238:
235:
234:
232:
228:
225:
224:
216:
215:
214:
211:
210:
208:
207:
199:DTXSID10436194
194:
192:
180:
177:
176:
174:
173:
165:
163:
157:
156:
154:
153:
145:
143:
135:
132:
131:
129:
128:
120:
118:
112:
111:
108:
107:Abbreviations
104:
103:
101:
100:
92:
90:
83:
80:
79:
77:
76:
68:
66:
61:
58:
57:
53:
52:
49:
45:
44:
40:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1062:
1051:
1048:
1046:
1043:
1042:
1040:
1029:
1025:
1018:
1014:
1007:
1003:
1002:
998:
989:
985:
981:
977:
973:
969:
968:
960:
957:
952:
948:
944:
941:
940:
939:J. Org. Chem.
931:
928:
923:
919:
915:
912:
911:
910:J. Org. Chem.
903:
900:
895:
889:
881:
879:0-12-701060-2
875:
871:
867:
863:
857:
854:
849:
845:
841:
838:
837:
836:J. Org. Chem.
829:
826:
821:
815:
812:
807:
803:
799:
796:
795:
787:
784:
778:
771:
765:
758:
757:
752:
745:
742:
739:
735:
729:
726:
721:
717:
713:
710:
709:
696:
690:
688:
684:
679:
673:
670:
663:
658:
654:
653:
652:
650:
646:
642:
639:to introduce
638:
634:
630:
626:
622:
619:
615:
611:
607:
603:
599:
591:
589:
587:
583:
579:
576:
572:
568:
567:Brønsted base
556:
551:
523:
501:
500:
499:
498:
494:
490:
482:
480:
478:
475:
470:
468:
464:
460:
456:
452:
448:
447:dimsyl sodium
444:
441:(also called
440:
428:
421:
416:
399:
393:
390:
386:
383:
378:
377:
372:
368:
364:
359:
358:
354:
353:
348:
343:
339:
335:
333:
330:
329:
325:
322:
318:
317:
313:
310:
309:
305:
303:
300:
299:
287:
284:
280:
279:
274:
265:
261:
254:
243:
233:
223:
219:
212:
204:
200:
196:
195:
193:
183:
179:
178:
171:
167:
166:
164:
162:
159:
158:
151:
147:
146:
144:
138:
134:
133:
126:
122:
121:
119:
117:
114:
113:
109:
106:
105:
98:
94:
93:
91:
87:
82:
81:
74:
70:
69:
67:
64:
60:
59:
54:
46:
38:
34:
29:
25:
20:
1030:. June 2009.
1017:the original
971:
965:
959:
942:
937:
930:
913:
908:
902:
868:. New York:
865:
862:Trost, B. M.
856:
839:
834:
828:
814:
797:
792:
786:
776:
764:cite journal
754:
744:
728:
711:
706:
695:Corey, E. J.
672:
648:
641:nucleophiles
632:
624:
609:
605:
595:
560:
493:sodium amide
486:
476:
471:
446:
442:
438:
437:
361:Main hazards
350:
56:Identifiers
48:Other names
643:alpha to a
629:elimination
483:Preparation
467:nucleophile
355:(OHS/OSH):
326:decomposes
311:Appearance
296:NaOS
276:Properties
1039:Categories
664:References
571:phosphorus
510:+ NaH → CH
332:Solubility
302:Molar mass
170:R6HI470Q52
116:ChemSpider
84:3D model (
73:15590-23-5
63:CAS Number
967:Synthesis
888:cite book
800:: 53–64.
598:condenses
557:As a base
552:Reactions
988:95643470
645:carbonyl
345:Hazards
150:10154010
621:ketones
596:NaDMSO
544:Na + NH
420:what is
418: (
267:.O=S()C
137:PubChem
125:8329518
110:NaDMSO
986:
876:
701:-SO-CH
618:methyl
616:gives
602:esters
578:ylides
575:sulfur
561:The pK
532:+ NaNH
518:Na + H
477:et al.
443:NaDMSO
415:verify
412:
260:SMILES
31:Names
1020:(PDF)
1009:(PDF)
984:S2CID
600:with
474:Corey
461:as a
218:InChI
86:JSmol
972:1985
894:link
874:ISBN
770:link
584:and
573:and
540:SOCH
536:→ CH
528:SOCH
514:SOCH
506:SOCH
497:DMSO
465:and
463:base
367:NaOH
338:DMSO
161:UNII
976:doi
947:doi
918:doi
844:doi
802:doi
734:doi
716:doi
651:).
495:in
491:or
453:of
445:or
187:EPA
140:CID
1041::
1011:.
982:.
970:.
943:46
914:54
890:}}
886:{{
872:.
840:57
798:59
774:;
766:}}
762:{{
753:.
712:87
686:^
588:.
524:CH
502:CH
469:.
387:,
990:.
978::
953:.
949::
924:.
920::
896:)
882:.
850:.
846::
822:.
808:.
804::
781:.
772:)
736::
722:.
718::
703:2
699:3
680:.
649:5
647:(
633:4
625:3
623:(
610:2
606:1
604:(
563:a
546:3
542:2
538:3
534:2
530:3
526:3
520:2
516:2
512:3
508:3
504:3
410:N
294:5
292:H
290:2
288:C
189:)
185:(
88:)
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