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University of Illinois at Urbana-Champaign

Synthesis and Use of a Tetradentate Ligand With C4v Symmetry: 1alpha, 2alpha, 3alpha, 4alpha-Tetrahydroxy- 1beta, 2beta, 3beta, 4beta-Tetramethylcyclobutane

Abstract

dc:description

The synthesis and photochemistry is described for several enediol derivatives designed as possible precursors of a cyclobutane-based tetradentate ligand of C$\sb{\rm 4v}$ symmetry. A new synthetic dehydrogenation reaction to form carbon-carbon double bonds, using the in situ combination of potassium tert -butoxide and tert -butyl hypochlorite, is presented. The stereospecific intramolecular photodimerization of an enediol pyrophosphate is described. Hydrolysis of the photoproduct from this reaction gives 1α,2α,3α,4α-tetrahydroxy-1β,2β,3β,4β-tetramethylcyclobutane, 1, a tetradentate ligand with C$\sb{\rm 4v}$ symmetry.

Degree

thesis:*
Name thesis:degree_name
Ph.D.
Level thesis:degree_level
Dissertation
Discipline thesis:degree_discipline
Chemistry
Grantor
University of Illinois at Urbana-Champaign
Year dc:date
2014

Author and committee

dc:creator, dc:contributor.*
Author dc:creator
  • Kahle, Charles Franz, Ii

Subjects

dc:subject × 1

Identifiers

dc:identifier.*
Identifier
(UMI)AAI8721670
OAI identifier oai:identifier
oai:www.ideals.illinois.edu:2142/70371

Chain of custody

source
Harvested from
University of Illinois - Urbana-Champaign
Base URL
www.ideals.illinois.edu/oai-pmh
Last updated
2026-07-22
Source record
OAI-PMH GetRecord
citation

Kahle, Charles Franz, Ii. Synthesis and Use of a Tetradentate Ligand With C4v Symmetry: 1alpha, 2alpha, 3alpha, 4alpha-Tetrahydroxy- 1beta, 2beta, 3beta, 4beta-Tetramethylcyclobutane. Dissertation thesis, University of Illinois at Urbana-Champaign, 2014. http://hdl.handle.net/2142/70371