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Amidoalkylation of phosphorus trichloride with acetamide and functionalized cyclic ketones-evidence of dominating role of side-reactions.
Autorzy
Rok wydania
2014
Czasopismo
Phosphorus, Sulfur, and Silicon and the Related Elements
Numer woluminu
189
Strony
1068-1075
DOI
10.1080/10426507.2014.905573
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The course of the reaction between phosphorus trichloride, acetamide and ethyl oxoalkanecarboxylates was studied in terms of the production of side-products. When ethyl 2-oxocycloalkane- and 4-oxocyclohexanecarboxylates were used as substrates, not only mixtures of the expected products—aminophosphonocycloalkanecarboxylic acids and their ethyl esters but also the formation of three side-products, namely 1-aminocycloalkanephosphonic acids (products of decarboxylation of the latter ones) and 1-aminoethane-1,1-diphosphonic and 1-hydroxyethane-1,1diphosphonic acids (products of the reaction of substrate and solvent with phosphonylating agent) were observed. Ethyl 2-oxo-cyclooctanecarboxylate afforded the expected 2-amino-2-pohosphonocyclooctanecarboxylic acid in minute amounts. For comparison reactions of 1-butyloxocarbonyloxopiperidines afforded the desired aminopiperidinephosphonic acids in good yields and without formation of side-products.
Słowa kluczowe
phosphonic analoques aspartic and glutamic acids, aminophosphonates, Oleksyszyn-Soroka reaction, side products
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