Degree Type

Dissertation

Date of Award

1985

Degree Name

Doctor of Philosophy

Department

Chemistry

Abstract

Interest in the use of free radical reactions in synthetic organic chemistry has greatly intensified in recent years. A program was undertaken to develop a free radical synthesis of (gamma)-lactones which would occur under neutral conditions. Thus, treatment of olefins with tri-n-butylstannyl iodoacetate in the presence of a catalytic amount of the free radical initiator, 2,2'-azobis(2-methylpropionitrile) (AIBN) in refluxing benzene resulted in good yields of 4-substituted-(gamma)-lactones. The products were separated from iodotri-n-butylstannane by partitioning between acetonitrile and hexanes. Further purification by column chromatography afforded the pure (gamma)-lactones;This reaction has also been extended to the synthesis of bicyclic lactones via the intramolecular cyclizations of appropriately constructed tri-n-butylstannyl iodoesters under the same reaction conditions. The mild reaction conditions employed allow for the introduction of a variety of functional groups at the 4-position including alcohols, ethers, and even alkylsilanes and silyl ethers.

DOI

https://doi.org/10.31274/rtd-180813-8698

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/

Copyright Owner

Kevin Dean Landgrebe

Language

en

Proquest ID

AAI8604487

File Format

application/pdf

File Size

93 pages

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