38:
447:
258:
28:
687:
615:
890:
Reider, Paul J.; Davis, Paul; Hughes, David L.; Grabowski, Edward J. J. (1987). "Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist".
918:
Chandra, Devesh; Dhiman, Ankit K; Kumar, Rakesh; Sharma, Upendra (2019). "Microwave-Assisted Metal-Free Rapid
Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reactiont".
826:"Preparation of Enatiomerically Pure Decahydro-6H-isoquino[2,1-g][1,6]naphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzo[a]quinolizinone Resolution"
699:, deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally, semipinacol rearrangement to re-establish the ketone function.
628:
486:
666:, it is a relatively strong acid that is a colorless solid at room temperature and is soluble in water and a wide variety of organic substances.
147:
140:
27:
695:
Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-
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was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure
725:. Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as
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742:
111:
92:
762:
Bartlett, Paul D.; Knox, L. H. (1965). "D,L-10-Camphorsulfonic acid (Reychler's Acid)".
470:
InChI=1S/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14)
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741:. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution of
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715:
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This compound is commercially available. It can be prepared by sulfonation of
545:
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Clark, Robin D.; Kern, John R.; Kurz, Lilia J.; Nelson, Janis T. (1990).
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Except where otherwise noted, data are given for materials in their
170:
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Charette, André B. (2001). "3-Bromocamphor-8-sulfonic Acid".
721:
Camphorsulfonic acid is also being used for the synthesis of
430:
36:
26:
61:(7,7-dimethyl-2-oxobicycloheptan-1-yl)methanesulfonic acid
710:
for chiral amines and other cations. The synthesis of
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Advanced organic chemistry : reaction mechanisms
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859:Encyclopedia of Reagents for Organic Synthesis
70:Reychler's acid; 2-Oxobornane-10-sulfonic acid
8:
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15:
841:
706:, CSA and its derivatives can be used as
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31:Wireframe model of camphorsulfonic acid
795:. San Diego: Harcourt/Academic Press.
247:
473:Key: MIOPJNTWMNEORI-UHFFFAOYSA-N
178:
7:
301:
14:
613:
526:
499:O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C
494:CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
609:(at 25 °C , 100 kPa).
538:
532:
520:
1:
791:Brückner, Reinhard (2002).
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861:. John Wiley & Sons.
697:semipinacol rearrangement
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867:10.1002/047084289X.rb283
778:10.15227/orgsyn.045.0012
650:, sometimes abbreviated
290:10-Camphorsulfonic+acid
933:10.1002/ejoc.201900325
739:lanabecestat camsylate
690:
41:
32:
735:trimetaphan camsilate
689:
660:organosulfur compound
40:
30:
17:Camphorsulfonic acid
648:Camphorsulfonic acid
563:195 °C (decomposes)
57:Preferred IUPAC name
905:10.1021/jo00381a052
843:10.3987/COM-89-5250
553: g·mol
160:Beilstein Reference
18:
921:Eur. J. Org. Chem.
691:
636:Infobox references
42:
33:
16:
927:(16): 2753–2758.
765:Organic Syntheses
704:organic synthesis
644:Chemical compound
642:
641:
592:Safety data sheet
426:CompTox Dashboard
148:Interactive image
141:Interactive image
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679:acetic anhydride
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598:External MSDS
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830:Heterocycles
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733:, including
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76:Identifiers
68:Other names
508:Properties
254:100.025.024
180:CHEBI:55379
876:0471936235
836:(2): 353.
749:References
723:quinolines
716:devazepide
546:Molar mass
399:9TLZ01S15L
387:Y6075I4FXE
380:D8D049375Q
191:ChemSpider
128:3D model (
100:35963-20-3
83:CAS Number
941:107383202
811:269472848
731:camsylate
727:camsilate
712:osanetant
415:UN number
275:227-527-0
267:EC Number
112:3144-16-9
93:5872-08-2
955:Category
586:Hazards
402: (1
390: (1
358: (4
346: (4
343:43833349
334: (1
322: (1
234: (4
222: (1
210: (1
165:2216194
115: (1
103: (1
671:camphor
629:what is
627: (
569:Acidity
355:3057042
299:PubChem
231:2318313
939:
873:
809:
799:
772:: 12.
658:is an
656:10-CSA
624:verify
621:
594:(SDS)
551:232.29
487:SMILES
331:218580
319:131278
219:189449
207:116050
51:Names
937:S2CID
673:with
462:InChI
419:1759
312:18462
200:17438
171:ChEBI
130:JSmol
925:2019
871:ISBN
807:OCLC
797:ISBN
737:and
677:and
581:1.2
371:UNII
284:MeSH
929:doi
901:doi
863:doi
838:doi
774:doi
729:or
702:In
654:or
652:CSA
431:EPA
302:CID
957::
935:.
897:52
869:.
834:31
832:.
828:.
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770:45
768:.
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571:(p
530:16
524:10
943:.
931::
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903::
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865::
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840::
813:.
781:.
776::
619:N
576:a
573:K
539:S
536:4
533:O
527:H
521:C
433:)
429:(
406:)
404:S
394:)
392:R
362:)
360:S
350:)
348:R
338:)
336:S
326:)
324:R
238:)
236:S
226:)
224:S
214:)
212:R
132:)
119:)
117:S
107:)
105:R
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