Chemistry of acetylenic ethers 63: The synthesis of α,β‐unsaturated thiolesters from carbonyl compounds, acetylenic thioethers, and boron trifluoride
- 1 January 1963
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 82 (2) , 157-171
- https://doi.org/10.1002/recl.19630820208
Abstract
The α,β‐unsaturated thiolesters listed in Table I have been prepared by treating a mixture of a carbonyl compound and boron trifluoride with an acetylenic thioether (see reaction scheme 2). Good yields are obtained when ethers are used as solvents. The configuration of the esters prepared from aldehydes is trans. From unsymmetrical ketones mixtures of cis and trans isomers are formed.Keywords
This publication has 15 references indexed in Scilit:
- Chemistry of acetylenic ethers. LXI: A simple method for the preparation of acetylenic thioethers, selenoethers and telluroethers (Preliminary publication)Recueil des Travaux Chimiques des Pays-Bas, 1962
- Mechanism of reactions of unsaturated ethers and thioethers IV: Acid catalyzed rearrangement of ethoxyethynyl- and ethylthioethynyl-carbinolsRecueil des Travaux Chimiques des Pays-Bas, 1961
- 1-Methoxyvinyl Esters.1 I. Preparation and PropertiesJournal of the American Chemical Society, 1960
- Chemistry of acetylenic ethers XLI. Condensation of acetylenic ethers with carbonyl compounds under anhydrous conditions; direct formation of α,β‐unsaturated esters: (preliminary communication)Recueil des Travaux Chimiques des Pays-Bas, 1959
- Steroid Acids and their Transformation Products. I. Thiol Esters1aJournal of the American Chemical Society, 1948
- Reformatzky reactions with s‐methyl‐bromothioacetateRecueil des Travaux Chimiques des Pays-Bas, 1947
- A New Aldehyde Synthesis1Journal of the American Chemical Society, 1946
- On the Structure of Dimethyl Ether-Boron TrifluorideJournal of the American Chemical Society, 1945
- Donor-Acceptor Bonding. II. An Electron Diffraction Investigation of the Structure of Dimethyl Ether-Boron TrifluorideJournal of the American Chemical Society, 1943
- The Preparation and Properties of a Series of Alkyl Thiolacetates1Journal of the American Chemical Society, 1937