Amidoalkylation of Phosphorus Trichloride with Acetamide and Alkyl Oxocycloalkanecarboxylates

Abstract

The course of the reaction between phosphorus trichloride, acetamide, and ethyl oxoalkanecarboxylates was studied in terms of the production of side-products. When alkyl 2-oxocycloalkanecarboxylates were used as substrates, together with the expected products—2-amino-2-phosphonocycloalkanecarboxylic acids—three side-products, namely 1-aminocycloalkanephosphonic acids (decarboxylation products of the latter compounds), 1-aminoethane-1,1-diphosphonic acids, and 1-hydroxyethane-1,1-diphosphonic acids were identified. Ethyl 1-oxocycloalkanecarboxylate afforded 4-amino-4-phosphonocyclohexane carboxylic acid in good yield.

Keywords:

• Aminophosphonates
• analogs of aspartic and glutamic acids
• Oleksyszyn–Soroka reaction

Dedicated to Professor Marian Mikołajczyk from the CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

This work was supported by Polish Ministry of Science and Higher Education.