Soluble polyethylene- and polystyrene-bound tin halides as catalysts for reductions of alkyl and aryl bromides and iodides by sodium borohydride

Journal Article · Fri Oct 13 04:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00282a034· OSTI ID:7156344

Bergbreiter, D E; Walker, S A ^[1]

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1. Texas A and M Univ., College Station (USA)

The synthesis, characterization, and use of soluble polyethylene- and polystyrene-bound tin chlorides as catalysts for the reduction of alkyl halides using a suspension of sodium borohydride in toluene and a crown ether as a phase-transfer catalyst are described. These tin-containing soluble macromolecules were synthesized by anionic oligomerization of ethylene or styrene followed by electrophilic substitution of the resulting living oligomer with various organic tin halides including tin tetrachloride, n-butyltin trichloride, di-n-butyltin dichloride, and diphenyltin dichloride. The resulting oligomer-bound tin reagents were characterized by {sup 1}H and {sup 119}Sn NMR spectroscopy, and the tin content of the oligomers was analyzed by ICP analysis. Typically the tin reagents were used as cocatalysts (ca. 10%) along with 10-20% of a crown ether as a phase-transfer catalyst in reductions of primary, secondary, and aryl halides using a suspension of sodium borohydride in hot toluene at 110{degree}C. Kinetic studies showed that the reaction rate was dependent on the concentration of the tin catalyst and that secondary halides reacted slightly faster than primary halides.

• OSTI ID: 7156344
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:21; ISSN 0022-3263; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
BROMINE COMPOUNDS
CATALYSTS
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
HALIDES
HALOGEN COMPOUNDS
INFORMATION
IODIDES
IODINE COMPOUNDS
KINETICS
MATERIALS
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC POLYMERS
PETROCHEMICALS
PETROLEUM PRODUCTS
PLASTICS
POLYETHYLENES
POLYMERS
POLYOLEFINS
POLYSTYRENE
POLYVINYLS
SYNTHETIC MATERIALS
TIN COMPOUNDS
TIN HALIDES