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The reaction of a number of (trialkylstannyl)copper reagents with 2-alkynoates, N,N-dimethyl-2-alkynaraides and 1-alkynes is described. It has been found that the (trimethylstannyl)copper reagents 14 and 43-46 efficiently transfer the trimethylstannyl group to oc-alkynoates. Reagent 14 (THF, -48°C) provided predominantly the (Z)-3-trimethyl-stannyl-2-alkenoate (22), reagents 44 and 45 (THF, -48°C) afforded essentially exclusively the corresponding (E) isomer 21, while reagents 43 and 46 gave a mixture of isomers. Using the above methodology, ethyl 2-pentynoate was converted into either (Z)- or (E)-3-( tri-n-butylstannyl)-2-pentenoate. The (E) isomer was converted into the vinylstannane 188 which was transformed (MeLi, THF, -20°C) into the corresponding stereochemically homogeneous vinyllithium reagent and elaborated into the acyl portion of (±)-triophamine (172), a diacylguanidine recently isolated from Triopha catalinae. Reaction of 2-alkynoates with excess 44 or 45 (THF, 0°C) afforded, as essentially the only products, (E)-2,3-bis(trimethyl-stannyl)-2-alkenoates (115). One member of this new class of compounds, ester 114 (=115, R = Me, R' = Et) was selectively transmetalated (MeLi, THF, -98°C) and the resultant nucleophilic species was allowed to react with a number of reactive electrophiles to produce esters of general structure 141. / Science, Faculty of / Chemistry, Department of / Graduate

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Thesis (Ph. D.)--University of Wisconsin--Madison, 1962. / Typescript. Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references.

Thesis (M. Phil.)--University of Hong Kong, 1984. / Caption title.

published_or_final_version / Chemistry / Master / Master of Philosophy

Thesis (Ph. D.)--Dept. of Physical and Inorganic Chemistry, University of Adelaide, 1989. / Typescript (Photocopy). Includes bibliographical references.

Thesis (Ph. D.)--Florida State University, 2005. / Advisor: Igor V. Alabugin, Florida State University, College of Arts and Sciences, Dept. of Chemistry and Biochemistry. Title and description from dissertation home page (viewed Jan. 25, 2006). Document formatted into pages; contains xvi, 346 pages. Includes bibliographical references.

Thesis (Ph. D.)--University of Texas at Austin, 2000. / Vita. Includes bibliographical references. Available also in a digital version from Dissertation Abstracts.

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