1,3-Dioxolan-4-ones and 1,3-oxathiolan-5-ones. Configuration of cis and trans isomers |
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Authors: | Kurt Pilgram Mike Zupan |
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Abstract: | The attempted acid-catalyzed azeotropic removal of water from a mixture containing lactamide and chloral in refluxing toluene lead to the elimination of ammonia; both cis- and trans-5-methyi-2-(trichloromethyl)-1,3-dioxolan-4-one were isolated. A number of 1,3-dioxolan-4-ones and 1,3-oxathiolan-5-ones were obtained by cyclodehydration of aldehydes with α-hydroxy- and α-mercapto-carboxylic acids in the presence of boron trifluoride etherate. Geometric isomers were separated, and their configurations were determined by nuclear magnetic resonance. |
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