We demonstrate here that a new pyrene-supported tin hydride can be used in radical chemistry. Final products were easily purified by adsorption of the PAH-supported tin side product with activated carbon.
A water soluble tin hydride reagent
β Scribed by James Light; Ronald Breslow
- Book ID
- 104222230
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 142 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A water soluble tin hydride has been synthesized carrying three methoxyethoxypropyl groups. It reduces various alkyl halides in water, or in organic solvents.
Tin hydride radical chemistry is widely used,1 but the solubility of tri-n-butyl tin hydride limits it to organic solvents. In order to perform tin radical chemistry in water, we designed and synthesized tin hydride 5. This is sufficiently soluble in water (ca. 30 mM at r.t., more on warming) to reduce alkyl halides under free radical conditions. It is also nonvolatile and odorless.
π SIMILAR VOLUMES
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Rate constants for 6-exo cyclization of the 7,7-diphenyl-6-heptenyl radical (3) in benzotrifluoride (BTF, PhCF3) were determined by laser flash photolysis, and radical clock 3 was used in competition kinetic studies for determination of rate constants of reactions of the fluorous tin hydride reagent