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
Copyright Date
1985
Language
en
Proquest ID
AAI8604487
File Format
application/pdf
File Size
93 pages
Recommended Citation
Landgrebe, Kevin Dean, "A free radical synthesis of Y-lactones using tri-n-butylstannyl iodoesters " (1985). Retrospective Theses and Dissertations. 8717.
https://lib.dr.iastate.edu/rtd/8717
