Palladium (II) Mediated Transformation: Exploring Synthetic Methodology for the Synthesis of Cyclopentenones from Tertiary-Cyclobutanois
type: CreativeWork
description: A new method for the synthesis of ring-fused cyclopentenone is described. The method utilizes the built-in strain of tertiary cyclobutanol to drive the palladium(II)-catalyzed rearrangement to the corresponding ring-fused cyclopentanone followed by Saegusa-Ito reaction to furnish final cyclopentenone product. Extensive efforts to transform this reaction into a catalytic process by screening various palladium(II) sources, ligands, oxidants, bases, solvents and reaction temperatures failed. Interesting and unexpected results were however obtained while exploring copper(II) chloride and copper(II) bromide as potential oxidants.
abstract: A new method for the synthesis of ring-fused cyclopentenone is described. The method utilizes the built-in strain of tertiary cyclobutanol to drive the palladium(II)-catalyzed rearrangement to the corresponding ring-fused cyclopentanone followed by Saegusa-Ito reaction to furnish final cyclopentenone product. Extensive efforts to transform this reaction into a catalytic process by screening various palladium(II) sources, ligands, oxidants, bases, solvents and reaction temperatures failed. Interesting and unexpected results were however obtained while exploring copper(II) chloride and copper(II) bromide as potential oxidants.
author: Nikolaev, Andrei
language: en
keywords: Chemistry
date published: 2015-08-28
date modified: 2026-07-24T06:33:49Z
provider: York University
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: York University

PropertyValue
property ID: Handle
value: http://hdl.handle.net/10315/30036