Fragmentation of trimethylsilyl derivatives of 2-alkoxyphenols: a further violation of the ‘even-electron rule’
The mass spectra of trimethylsilyl (TMS) ethers of 2-methoxyphenols show abundant [M-30]+˙ 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-hy...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
October 1985
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| In: |
Organic mass spectrometry
Year: 1985, Volume: 20, Issue: 10, Pages: 614-618 |
| ISSN: | 2376-3884 |
| DOI: | 10.1002/oms.1210201005 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/oms.1210201005 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/oms.1210201005 
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| Author Notes: | Dietlinde Krauss, Hans Georg Mainx, Bernhard Tauscher and Peter Bischof |
| Summary: | The mass spectra of trimethylsilyl (TMS) ethers of 2-methoxyphenols show abundant [M-30]+˙ 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 a methyl group with rearrangement and hydrogen migration is competitive. |
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| Item Description: | Gesehen am 16.12.2025 |
| Physical Description: | Online Resource |
| ISSN: | 2376-3884 |
| DOI: | 10.1002/oms.1210201005 |