The Journal of Organic Chemistry

Torsional barriers in quinolinone hydroxylamine and sulfenamide derivatives

M Raban, VA Martin, L Craine

Index: Raban, Morton; Martin, A. Van; Craine, Leslie Journal of Organic Chemistry, 1990 , vol. 55, # 44 p. 4311 - 4316

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Citation Number: 9

Abstract

The preparation of a 2-quinolinone hydroxylamine (N-(benzyloxy)-2 (LH)-quo~ one) and sulfenamide derivatives of 2-and 4-quinolinone (N-[(2, 4-dinitrophenyl) thio]-3-benzyl-4- methyl-2 (l~-quinolinone and N-[(2, 4-dinitro-phenyl) thio]-3-benzyl-2-methyl-4 (lH)- quinolinone) are described. All three compounds exhibited chemical shift nonequivalence of diastereotopic benzyl methylene hydrogens, indicative of hindered rotation about the N-0 ...