15964-84-8Relevant academic research and scientific papers
Fragmentation of Trimethylsilyl Derivatives of 2-Alkoxyphenols: a Further Violation of the 'Even-electron Rule'
Krauss, Dietlinde,Mainx, Hans Georg,Tauscher, Bernhard,Bischof, Peter
, p. 614 - 618 (2007/10/02)
The mass spectra of trimethylsilyl (TMS) ethers of 2-methoxyphenols show abundant +* ions originating from consecutive loss of two methyl radicals.This is illustrated by comparison of the accurate mass-measured and linked-scan spectra of the TMS derivatives of 2-methoxyphenol (guaiacol), 4-hydroxy-3-methoxybenzaldehyde (vanillin) and 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester (ferulic acid methyl ester) with those of the TMS derivatives of phenol, 4-hydroxybenzaldehyde, 3-(4-hydroxyphenyl)-2-propenoic acid methyl ester (p-coumaric acid methyl ester), 3-methoxyphenol and 4-methoxyphenol.This distinctive ortho effect is valuable in the identification of isomeric phenolic compounds.In the spectra of the TMS derivatives of 2-ethoxyphenol and 2-propoxyphenol the sequential loss of two radicals is less pronounced, because elimination of the side-chain and methyl group with rearrengement and hydrogen migration is competitive.
