Bridges, Alexander J.
M.S. (Master of Science)
Department of Chemistry
Allene; Organometallic compounds
3-Methy1-1-phenylthio-1-trimethylsilylbuta-1,2-diene reacts with different alkyl-lithiums reagents by C-Si or C-S bond cleavage, rather than by Michael addition or metalation. The C-S bond cleavage product (induced by t-butyl lithium), l-lithio-3-methyl-1-trimethylsilylbuta-1,2-diene is alkylated mainly γ with carbonyl compounds, but is silylated α with Et₃SiCl to form a 1,1-bis-silylallene. The dimerization properties of the α-silyl-α-lithioallene were also examined. By judicious selection of conditions it was possible to produce diallene, allene acetylene and diacetylene dimers. The oxidation of 3-Methyl-1-phenylthio-1-trimethylsilyl-buta-l,2-diene to the corresponding sulfoxide and its subsequent Silyl-Pummerer rearrangement were studied.
Fedij, Victor, "Metalation studies on highly substituted allenes" (1984). Graduate Research Theses & Dissertations. 3951.
viii, 77 pages
Northern Illinois University
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