TAUTOMERISM AND VAPOR-PHASE TRANSFORMATIONS OF 2-HYDROXYTETRAHYDROFURAN

Authors

  • А. Лебедев Latvian Institute of Organic Synthesis
  • Л. Лейте Latvian Institute of Organic Synthesis
  • М. Флейшер Latvian Institute of Organic Synthesis
  • В. Стонкус Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/258

Keywords:

2-hydroxytetrahydrofuran, 4-hydroxybutanal, 2, 3-dihydrofuran, tautomerism, dehydration, AM1 method, concerted mechanism

Abstract

The relative stability of 2-hydroxytetrahydrofuran and the tautomeric 4-hydroxybutanal was determined by the semi-empirical AM1 method. It was concluded that the cyclic tautomer predominates in the gas phase at 25°C. Vapor-phase dehydration of 2-hydroxytetrahydrofuran in the presence of porcelain and silica gel L leads to a quantitative yield of 2,3-dihydrofuran.

Authors: A. Lebedev, L. Leite, M. Fleisher, and V. Stonkus.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (7), pp 775-778

http://link.springer.com/article/10.1007/BF02256908

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Published

2013-02-06

Issue

No. 7 (2000)

Section

Original Papers