Date of Award

4-1978

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Supervisor

Professor Nick H. Werstiuk

Abstract

The stereochemistry of acid-catalyzed ring-opening of the cyclopropane ring in nortricyclane, 4-chloronortricyclane and 4-bromonortricyclane in D₂SO₄/acetic acid-d₄ medium has been investigated. Stereochemical analysis was carried out by dmr spectroscopy. The endo:exo deuterium ratios, at C6 of the exo-2-norbornyl trideuteroacetates-d1 are 1.12, 1.35 and 1.61 respectively.

These results conclusively establish that the norbornyl cation formed by edge-protonation is an unsymmetrical, classical and rapidly equilibrating species and not a symmetrical non-classical σ-bridged species.

Files over 3MB may be slow to open. For best results, right-click and select "save as..."

Included in

Chemistry Commons

Share

COinS