Pyrolyse und Massenspektren von 5-(Hydroxyphenoxymethyl)-2-oxazolidinon und p- oder m-Bis(2-oxooxazolidin-5-ylmethoxy)benzol

Abstract

Abstract 5-(Hydroxyphenoxymethyl)-2-oxazolidinone (1) and p- or m-bis(2-oxooxazolidin-5-ylmethoxy)benzene (2 or 3) were prepared by the reaction of tris(2,3-epoxypropyl)-1,3,5-triazin-2,4,6(1H,3H,5H)-trione with hydroquinone and resorcinol. These compounds were found by the thermal analysis to be thermally stable. The activation energies of the pyrolysis for 1, 2, and 3 were calculated from the DTA curves to be 142.7, 158.8, and 130.0 kJ mol−1, respectively. The mechanism of the main fragmentation of the linkages between the benzene and oxazolidinone rings by electron impact was found to consist of two processes; a simple cleavage and a rearrangement reaction. Further, each process had the three cleavage modes. In mass spectra of 2 and 3, the fragment ion which corresponded to the molecular ion peak for 1 was detected. High resolution mass spectrometry established the composition of many peaks in the low resolution spectra of the compounds studied.