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| Sodium methylsulfinylmethylide | |
|---|---|
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| IUPAC name | Sodium methylsulfinylmethylide |
| Other names | sodium dimsylate, dimsylsodium, NaDMSYL |
| Identifiers | |
| Abbreviations | NaDMSO |
| CAS number | 15590-23-5 |
| Properties | |
| Molecular formula | C2H5NaOS |
| Molar mass | 100.13 |
| Solubility in water | Reactive |
| Solubility in DMSO | Soluble |
| Related compounds | |
| Related compounds | Dimethyloxosulfonium methylide |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Sodium methylsulfinylmethylide (also called NaDMSO) is the conjugate base of dimethyl sulfoxide. It has several uses in organic chemistry as a base and nucleophile.
Since the first publication in 1965 by Corey et al.1, a large number of publications have described additional uses for this reagent.2
Contents |
Preparation
Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide3 in DMSO at 70 °C for 1 hr.
- CH3SOCH3 + NaH → CH3SOCH2−Na+ + H2
- CH3SOCH3 + NaNH2 → CH3SOCH2−Na+ + NH3
Applications
As a Base
The pKa of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides.4 NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.15
As a Nucleophile
Reaction with esters
NaDMSO will condense with esters (1) to form β-ketosulfoxides (2), which have been shown to be very useful synthetic intermediates.6 Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones (3).7 Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones (4). Interestingly, β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl (5).8
References
- ^ a b Corey, E. J.; Chaykovsky, M. (1965). "Methylsulfinyl Carbanion (CH3-SO-CH2−). Formation and Applications to Organic Synthesis". J. Am. Chem. Soc. 87: 1345. doi:.
- ^ Durst, T. (1969). (review). Adv. Org. Chem. 6: 285.
- ^ 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". J. Organomet. Chem. 59: 53. doi:.
- ^ Romo, D.; Myers, A. I. (1992). "An asymmetric route to enantiomerically pure 1,2,3-trisubstituted cyclopropanes". J. Org. Chem. 57: 6265. doi:.
- ^ Trost, B. M.; Melvin, L. S., Jr. (1975). Sulfur Ylides: Emerging Synthetic Intermediates. New York: Academic Press.
- ^ 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". J. Org. Chem. 54: 5620. doi:.
- ^ 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". J. Org. Chem. 46: 4825. doi:.
- ^ Isibashi, H.; Okada, M.; Komatsu, H.; Ikeda, M. S. (1985). . Synthesis: 643.
External links
- "The Dimethyl Sulfoxide (DMSO) Anion — Dimsyl Ion". Gaylord Chemical Corporation (October 2007).
Wikipedia content modification information:
- This page was last modified on 10 October 2008, at 03:12.
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