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  • About
  • The Global ETD Search service is a free service for researchers to find electronic theses and dissertations. This service is provided by the Networked Digital Library of Theses and Dissertations.
    Our metadata is collected from universities around the world. If you manage a university/consortium/country archive and want to be added, details can be found on the NDLTD website.
1

The sodium borohydride reduction of organic halides and related derivatives in aprotic solvents

Vanderslice, Charles Warren January 1968 (has links)
Sodium borohydride reduces alkyl halides and their related tosylate derivatives in the order primary > secondary > tertiary, while the relative order of leaving-group ability is Ts⁻ ≥ I⁻ > Br⁻ > > Cl⁻. The yields obtained ranged from 90-100% for most simple, primary and secondary iodides, bromides, and tosylates, to 1-2% for the tertiary compounds. As in the case of the more reactive lithium aluminum hydride, the. reduction is believed to occur by an S<sub>N</sub>2 displacement on carbon. The reduction of a series of para-substituted benzyl chlorides revealed that the electronic effects of groups ranging from p-methoxy to p-nitro had a rather small effect on the rate of reduction. Aryl halides arc reduced by sodium borohydride in yields dependent upon the particular halogen involved, the presence of other ortho and para electron-withdrawing substituents, and the reaction temperature, among other factors. The same relative order of dehalogenation displayed by the alkyl halides was found. Polyhalomethanes such as carbon tetrachloride react with sodium borohydride to give the monohydro and dihydro compounds as the major products, the former predominating. The exact mechanism of the reduction is as yet undetermined, as water apparently catalyzes the reaction in some unknown manner. / Master of Science

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