Please use this identifier to cite or link to this item:
http://hdl.handle.net/11375/8509
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. |
Department: | Chemistry |
Keywords: | Chemistry;Chemistry |
Publication Date: | Apr-1978 |
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> |
URI: | http://hdl.handle.net/11375/8509 |
Identifier: | opendissertations/371 1243 887966 |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Size | Format | |
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fulltext.pdf | 5.01 MB | Adobe PDF | View/Open |
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