Carbohydrate Research

Determination of the gauche effect of 3-acetamido-and 3-acetoxy-piperidine and-tetrahydropyran by 1H-nmr spectroscopy

B Bernet, U Piantini, A Vasella

Index: Bernet, Bruno; Piantini, Umberto; Vasella, Andrea Carbohydrate Research, 1990 , vol. 204, # 1 p. 11 - 25

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Citation Number: 19

Abstract

Abstract The A-values of the acetamido and the acetoxy group were determined by low- temperature 1 Hn. mr spectroscopy. The limiting values for the relevant vicinal coupling constants of the newly prepared trans-(22) and cis-5-acetoxy-2-(1-hydroxy-1-methylethyl) tetrahydropyran (24) were obtained at room temperature. The attractive gauche effect of AcNH-3 and AcO-3 in piperidines, piperidinium trifluoroacetates, and tetrahydropyrans ...