Title

Generalized synthesis of [Gamma]-diketones

Abstract

Various synthetic schemes were explored in order to develop a general synthesis of γ-diketones. The addition of organometallic reagents to several γ-dicarboxylic acids and γ-dinitrile compounds failed to produce any ketonic product, whereas addition to γ-diesters and γ-diacid chlorides gave only small amounts of the diketones in a mixture of products. A series of γ-diketones was prepared in low to moderate yields by way of the corresponding acetylenic glycols. These glycols were made by treating acetylenedimagnesium bromide with various aldehydes and then hydrogenation to the saturated γ-dialcohols. Oxidation of the alcohols produced diketones of type RCOCH_2CH_2COR where R = ethyl, isopropyl, t-butyl, n-propyl, n-hexyl, phenyl and cyclohexyl radicals. Good yields of γ-diketones were obtained by dialkylating 2,2'-ethylenebis(m-dithiane) followed by hydrolysis. Except for isopropyl iodide, the alkylation was successful only with primary alkyl halides. Diketones of the above type where R = ethyl, isopropyl, n-propyl, isobutyl, n-butyl, isoamyl, and benzyl radicals were prepared.

Degree

PhD

College and Department

Chemistry and Biochemistry

Rights

http://lib.byu.edu/about/copyright/

Date Submitted

1970-06-01

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/Letd669

Keywords

[Gamma]-Diketones

Language

English

This document is currently not available here.

Share

COinS