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| SP - SULFONYL CHLORIDE RESIN, MP |
| PRODUCT: |
| SP –Sulfonyl Chloride,Resin, MP, a highly cross-linked polystyrene resin functionalized with a tosyl chloride end group. |
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| APPLICATIONS: |
- SP-Sulfonyl Chloride is a high-loaded resin with versatile scavenging applications.
- The resin can be used for the scavenging of various nucleophiles such as alcohols, amines, hydrazines and organometallics.
- The resin reacts with nucleophiles to give a variety of functional polymers which can be subsequently used as polymeric supports, reagents and catalysts in organic synthesis.
- SP-Sulfonyl Chloride can be employed in “Catch and Release” applications, wherein substrates are reacted with the resin to form an activated polymer intermediate, e.g. a polymer-bound tosylate with an alcohol.
- The polymeric intermediate, purified by simple washings, may be subjected to a second transformation that releases the product from the resin. This has been applied to synthesis of tertiary amines.
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| PROPERTIES: |
Resin Type: Macroporous poly(styrene-co-divinylbenzene)
Loading: 4.3-4.6 mmol/g (based on titration and elemental analysis)
Bead Size: 400-1100 microns, 20-40 mesh (>90% within) |
| Typical Scavenging: |
Resin (2.5 equiv relative to nucleophile), pyridine or triethylamine (20-30%),
3-5 h, at ambient temperature |
| Compatible Solvents: |
DCM, DCE, THF, DMF> |
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| REFERENCES: |
- Pirrung, M.C.; Tunney, L.N. J. Comb. Chem. 2000, 2, 675-680.
- Hansen,H.C.; Olsson,R.; Croston,G.; Andersson,C.-M. Bioorgan Med Chem Lett 2000, 10, 2435.
- Zhang, H.-C., Ye, H.; Moretto, A.F.; Brumfield, K.K.; Maryanoff, B.E. Org Letters 2000, 2, 89.
- Yoshida,Y.; Shimonishi,K.; Sakakura,Y.; Okada,S.; Aso,N.;Tanabe,Y. Synthesis 1999,9,1633-1636.
- Method for a-chlorination of ketones: Brummond,K.M.;Gesenberg,K.D.Tetrahedron Lett.1999,40, 2231.
- Takahashi, T.; Ebata, S.; Doi, T. Tetrahedron Lett. 1998, 39, 1369.
- Baxter, E. W; Rueter, J. K.; Nortey, S.O.; Reitz, A. B. Tetrahedron Lett. 1998, 39, 979.
- Rueter, J.K.; Nortey, S.O.; Baxter, E.W.; Leo, G.C.; Reitz, A.B.Tetrahedron Lett. 1998, 39, 975.
- Zhong, H.M.; Greco, M.N.; Maryanoff, B. E. J. Org. Chem., 1997, 62, 9326.
- Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998.
- For reviews on the use of polymer-supported arylsulfonyl chloride resin, see Huang, W.; He, B. Chill. J. Reactive Polymers (Engl.) 1992, 1, 61.
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