Title page for ETD etd-01122010-020317

Type of Document Dissertation
Author Kreh, Donald Willard
URN etd-01122010-020317
Title Selected reactions of some cyclic sulfoxides
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Vingiello, Frank A. Committee Chair
Brice, L. K. Jr. Committee Member
Krug, Robert C. Committee Member
Mason, John G. Committee Member
Wightman, James P. Committee Member
  • Cyclic compounds
Date of Defense 1966-04-05
Availability restricted

The previously unreported 3-methyltetrahydrothiophene I-oxide (1) and 3-methyl-2, 5-dihydrothiophene I-oxide (2) have been prepared by oxidation of the corresponding sulfides. The structure of these unsymmetric sulfoxides was established by chemical and physical methods. Nuclear magnetic resonance analyses have provided significant information concerning some stereochemical aspects of these molecules. In the case of 1. which has four possible configurations, both cis and trans isomers were shown to exist in the synthetic material. A study on the temperature dependence of the nuclear magnetic resonance spectrum of 2 between -34° and 100°, suggested little or no association of a dimeric nature between molecules of this unsaturated sulfoxide.

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