Date of Award
Chemistry and Biochemistry
CC BY-NC-ND 4.0
$\gamma$-Cationic-$\alpha,\beta$-unsaturated carbonyl synthons have been prepared via hexacarbonyldicobalt complexed $\gamma$-chloroalkynoates and alkynones (100). Treatment of 100 with silver salts in the presence of silyl enol ethers (102-104) generated 2-alkynyl-1,6-dicarbonyl compounds (134-149) in poor to good yields. Products of 101, with a non hydrogen substituent at the propargyl site, with 102 and 103 generated syn and anti diastereomers. The ratios of syn:anti diastereomers range from 1.3: 1 to 2.1: 1 for 102 to 6.9: 1 to 15: 1 for 103. These ratios are similar to literature compounds. Decomplexation to the alkyne effected in good to excellent yields. A dimer 151 was formed accidentally in poor yield with structural characteristics similar to compounds in its class. Source: Masters Abstracts International, Volume: 34-06, page: 2379. Adviser: J. R. Green. Thesis (M.Sc.)--University of Windsor (Canada), 1995.
Vizniowski, Charles Stephen., "Cobalt stabilized gamma-chloroalkynones and alkynoates as gamma-carbonyl cation synthons." (1995). Electronic Theses and Dissertations. 1455.