Date of Award

1-1-2011

Language

English

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

College/School/Department

Department of Chemistry

Content Description

1 online resource (xiv, 226 pages) : illustrations (some color)

Dissertation/Thesis Chair

Eric Block

Committee Members

Robert Brainard, Rabi Musah, Marina Petrukhina, Paul Toscano

Keywords

Characterization, Diallylic polysulfane, Synthesis, Thiarubrine E, Thiophene E, Antifungal agents, Hairy-root disease, Acetylene compounds, Plant metabolites, Polysulfides

Subject Categories

Chemistry | Organic Chemistry

Abstract

Garlic oil contains diallyl polysulfanes as major components, which have been used as environmentally benign bird repellants and nematicides. While previous studies found that the biological activity of polysulfanes increases with numbers of sulfur atoms, higher diallyl polysulfanes are currently unavailable. A simple approach was developed, using liquid sulfur as a reagent, to the synthesis of diallyl polysulfanes containing chains of more than 20 sulfur atoms. This method was successfully applied to other diallylic disulfides and to garlic oil to give new families of polysulfanes. Some diallyl polysulfanes were isolated in a pure form by preparative high performance liquid chromatography (HPLC) and characterized by nuclear magnetic resonance (NMR) spectroscopy. Those synthesized families of diallyl polysulfanes and garlic oil were also characterized by ultra performance liquid chromatography- (Ag+)-coordination ion spray-mass spectrometry (UPLC-Ag+-CIS-MS), and new members of families of silver-chelators were found in garlic oil.

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