Tetrahedron

X= Y-ZH compounds as potential 1, 3-Dipoles. Part 23 1, 2 mechanisms of the reactions of ninhydrin and phenalene trion with∝-amino acids. X-ray crystal structure of …

…, T Mongkolaussavaratana, S Thianpatanagul

Index: Grigg, Ronald; Malone, John F.; Mongkolaussavaratana, Theeravat; Thianpatanagul, Sunit Tetrahedron, 1989 , vol. 45, # 12 p. 3849 - 3862

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Citation Number: 31

Abstract

The ninhydrin reaction is shown to involve stereospecifically formed azomethine ylides of two types by trapping of the intermediates with maleimides as dipolarophiles. One type of azomethine ylide, in which the carboxyl group of theoriginal∝-amino acid is retained, is probably only important for glycine. The other type of azomethine ylide does not contain a carboxyl group and is formed from all ninhydrin positive∝-amino acids via ...