Collect. Czech. Chem. Commun. 2006, 71, 59-76

Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide

Wolf-Dieter Rudorfa,*, Dušan Loosb, Joanna Wybraniecc, Naďa Prónayovád, Ryszard Gawineckic and Zora Šustekováb

a Institute of Organic Chemistry, Martin-Luther-University, Kurt-Mothes-Str. 2, 06120 Halle, Germany
b Department of Organic Chemistry and Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovak Republic
c Department of Organic Chemistry, Academy of Technology and Agriculture, Faculty of Technology and Engineering, Seminaryjna 3, 85326 Bydgoszcz, Poland
d Central Laboratories, Faculty of Chemical Technology, Slovak Technical University, 812 37 Bratislava, Slovak Republic


Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, 13C NMR and AM1 semiempirical data.

Keywords: Malonates; N-Arylmalonamates; Ketene dithioacetals; AM1 calculations; Correlation analysis; Conformational analysis.

References: 21 live references.