Chemie von α??Aminonitrilen. 13. Mitteilung. Über die Bildung von 2??Oxoethyl??phosphaten (“Glycoladehyd??phosphaten”) aus rac??Oxirancarbonitril und …

…, E Pombo??Villar, A Eschenmoser

Index: Pitsch, Stefan; Pombo-Villar, Esteban; Eschenmoser, Albert Helvetica Chimica Acta, 1994 , vol. 77, # 8 p. 2251 - 2285

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Abstract

Oxiranecarbonitrile in basic acqueous solution at room temperature reacts regioselectively with inorganic phosphate to give the cyanohydrin of 2-oxoethyl phosphate ('glycolaldehyde phosphate'), a source of (the hydrate of) the free aldehyde, preferably in the presence of formaldehyde. In aqueous phosphate solution buffered to nearly neutral pH, oxiranecarbonitrile produces the phosphodiester of glycolaldehyde as its bis-cyanohydrin ...