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|Title:||Acid-Catalyzed Ring-Opening of 4-Halonortricyclanes. At Last a Solution to the Norbornyl Cation Problem|
|Authors:||Dhanoa, Singh Daljit|
|Advisor:||Werstiuk, Nick H.|
|Abstract:||<p>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.</p> <p>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.</p>|
|Appears in Collections:||Open Access Dissertations and Theses|
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