THERMAL RECYCLIZATION OF 2-ARYLSPIRO[3,1-BENZOXAZINE-4,1'-CYCLOPENTANES] IN THE GAS PHASE

Authors

  • Е. Г. Галкин Institute of Organic Chemistry, Ufa Science Center, Russian Academy of Sciences
  • А. С. Ерастов Institute of Organic Chemistry, Ufa Science Center, Russian Academy of Sciences
  • Е. М. Вырыпаев Institute of Organic Chemistry, Ufa Science Center, Russian Academy of Sciences
  • И. И. Фурлей Institute of Organic Chemistry, Ufa Science Center, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/837

Keywords:

2-arylspiro[3, 1-benzoxazine-4, 1'-cyclopentanes], N-[2-(cyclopent-1-en-1-yl)phenyl]aryl-amides, electron impact mass spectrometry, intramolecular recyclization, ionic mass chromatography, ring-chain equilibrium

Abstract

GC/MS analysis was used to study the thermal stability of 2-arylspiro[3,1-benzoxazine-4,1'-cyclopentanes] and isomeric N-[2-cyclopent-1-en-1-yl)phenyl]arylamides. Thermal isomerization of the benzoxazines to give arylamides on the chromatographic column was detected. Change in the ratio between peak intensities of the diagnostic [M]+ and [M-C2H5]+ ions allows to determine the ratio between open and cyclic forms. Heating up to 250°C at atmospheric pressure or prolonged storage of the benzoxazines also leads to their isomerization to arylamides in quantitative yield.

Authors: E. G. Galkin, A. S. Erastov, E. M. Vyrypaev, and I. I. Furley.

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (8), pp 1207-1211

http://link.springer.com/article/10.1007/s10593-013-1364-4

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Published

2013-08-13

Issue

No. 8 (2013)

Section

Original Papers