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The mechanisms of both ring-expansion reactions were investigated extensively, employing deuterium labelled methylenecyclopropyl amide substrates.The magnesium iodide-mediated ring expansions of secondary methylenecyclopropyl amides have been examined in detail. The scope of the previously reported rearrangement reaction has been successfully extended, permitting the synthesis of a library of heteroaryl-substituted 4-methyl-1,5-dihydro-pyrrol-2-ones. Development of a novel, complimentary synthetic procedure enabled access to the isomeric 4-methylene-pyrrolidin-2-one products.
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Adviser: Mark Lautens.
Thesis (M.Sc.)--University of Toronto, 2004.
Electronic version licensed for access by U. of T. users.
Source: Masters Abstracts International, Volume: 43-03, page: 0854.
MICR copy on microfiche (2 microfiches).
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