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1,3‐Dioxolan‐4‐ones and 1,3‐oxathiolan‐5‐ones. Configuration of cis and trans isomers
Author(s) -
Pilgram Kurt,
Zupan Mike
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140617
Subject(s) - chemistry , boron trifluoride , chloral , toluene , cis–trans isomerism , ammonia , walden inversion , medicinal chemistry , organic chemistry , catalysis
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.