Popkin, Matthew Edward; (1998) The development and application of new methods for the synthesis of organozinc carbenoids. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

This thesis concerns the generation of organozinc carbenoids and their subsequent reactions, particularly with alkenes to generate cyclopropanes. The thesis is divided into three major sections. The first section comprises a review of the current methods available for the direct cyclopropanation of alkenes. The review focuses on the more controlled methods, and in particular on the different classes of precursor suitable for cyclopropanation. The second chapter opens with an overview of the development of the generation of organozinc carbenoid via the reductive deoxygenation of carbonyl compounds. The generation of zinc carbenoids from a range of precursors is subsequently discussed in detail. The results are arranged to allow the reader to observe the chronological development of the chemistry. New observations on the formation of organozinc carbenoids from aldehydes and ketones are discussed first. The generation of organozinc carbenoids from acetals is then studied, and a series of new results presented. The generation of a novel class of α-alkoxyzinc carbenoids from simple orthoformates is then reported. A study into the generation of methylene organozinc carbenoids run concurrently with the aforementioned work is discussed and the chapter finishes with a brief insight into some attempts to generate other organozinc carbenoids and the range of unsuccessful precursors studied so far. A concluding chapter summarises the results of the work described above, and full experimental details together with appropriate references are appended.

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