Collect. Czech. Chem. Commun.
2006, 71, 709-722
https://doi.org/10.1135/cccc20060709
Preparation of 1-Adamantyl Ketones: Structure, Mechanism of Formation and Biological Activity of Potential By-Products
Robert Víchaa, Marek Nečasb and Milan Potáčekc,*
a Department of Food Engineering and Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Náměstí T.G.M. 275, 762 72 Zlín, Czech Republic
b Department of Inorganic Chemistry, Faculty of Science, Masaryk University Brno, Kotlářská 2, 611 37 Brno, Czech Republic
c Department of Organic Chemistry, Faculty of Science, Masaryk University Brno, Kotlářská 2, 611 37 Brno, Czech Republic
Abstract
Reactions between adamantane-1-carbonyl chloride and several Grignard reagents as well as interactions with solvents have been examined. Some new and unexpected adamantane derivatives were isolated, fully characterized and their biological activity determined. In particular, an unexpected isochromanone 16 was formed in an SEAr process, in which a stable hydrocarbon was the leaving group.
Keywords: Adamantane; 1-Adamantyl alkyl/aryl ketones; Acyl chlorides; Side products; Biological activity; Grignard reagents.
References: 40 live references.
