Article ID Journal Published Year Pages File Type
1236551 Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011 6 Pages PDF
Abstract

3β-Acetoxy-5α-cholestan-6-one semicarbazone 1 on reaction with hydrogen peroxide affords selectively 3β-acetoxy-5α-cholestan-6-spiro-1′,2′,4′-triazolidine-3′-one 2. The structural assignment of the product was confirmed by spectral data and elemental analysis. A free radical mechanism of the present reaction was described successfully by calculating theoretical models of 1, A, B and 2, using DFT with B3LYP/6-31G* basis set. It was found that the reaction undergoes through the formation of two radical intermediates and the only one isomer of the product in which –NH–CO– group is cis with respect C5α-H, was selectively obtained. Frontier molecular orbital, spin electronic density, electrostatic potential and atomic charges were discussed.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Preparation of 3β-acetoxy-5α-cholestan-6-spiro-1′,2′,4′-triazolidine-3′-one. ► Triazolidinone ring closes at C-6 carbon atom. ► Reaction mechanism is described by using density functional theoretical models.

Related Topics
Physical Sciences and Engineering Chemistry Analytical Chemistry
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