Di-tert-butylsilylene derivatives for the characterisation of bifunctional compounds by gas chromatography-mass spectrometry

Abstract

The cyclic di-tert-butylsilylene (DTBS) derivatives of diols, originally introduced as protecting groups, are suitable for analytical studies based on gas chromatography - mass spectrometry. Analogous derivatives are also preparable from other bifunctional substrates, exemplified here by β-hydroxy acids, alkylsalicylic acids and anthranilic acid. Useful Chromatographic separations of isomeric compounds are observed, whereas the mass spectra of the compounds studied here are much less distinctive, the preponderant fragmentations being those of silicon-alkyl bonds. Diols containing a tertiary hydroxylic group may be converted into DTBS derivatives by means of di-tert-butylsilyl ditriflate.