Abstract
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.
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