Reinvestigation of the acetalation of d-glucitol with acetone-zinc chloride

János Kuszmann, Pál Sohár, Gyula Horváth, Éva Tomori, Miklós Idei

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The acetonation of d-glucitol in the presence of zinc chloride has been studied in detail by gas-liquid chromatographic techniques. From among the 12 different peaks, those belonging to the 1,2:3,4:5,6-tri-, 1,2:3,5:4,6-tri-, 3,4:5,6-di-, 2,3:5,6-di-,1,2:3,4-di-, 1,2:5,6-di-, 1,2:4,6-di-, 1,2-mono-, 2,3-mono-, 3,4-mono-, and 5,6-mono-acetals could be identified. The course of the reaction was also studied by g.l.c. From the time-dependent ratio of the different acetals, it could be concluded that the reaction is kinetically controlled at the beginning, when terminal acetals are mainly formed. In the thermodynamically controlled equilibrium, reached after 5 days, the 1,2:3,4:5,6-tri- and the 2,3:5,6-di-acetal are present in almost equal proportions. The structure of the (new) 1,2:3,5:4,6-triacetal was established by mass-spectrometric and 13C-n.m.r. investigation.

Original languageEnglish
Pages (from-to)243-253
Number of pages11
JournalCarbohydrate Research
Volume79
Issue number2
DOIs
Publication statusPublished - Mar 1980

    Fingerprint

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this