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Hydrogen–carbon, carbon–carbon double rearrangement induced by proximity effects. Part 3: Essential structural requirements in methoxydiphenylmethanes

✍ Scribed by Leopoldo Ceraulo; Pasquale Agozzino; Mirella Ferrugia; Liliana Lamartina; Maria Concetta Natoli

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
267 KB
Volume
27
Category
Article
ISSN
1076-5174

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✦ Synopsis

The hydrogen-carbon, carbon-carbon double rearrangement, responsible for the formation of benzyl or tropylium ions previously observed in the electron ionization mass spectra of several substituted 1,lbis(dimethoxydipheny1)methanes bearing an ortho methoxy group, also occurs for 2-methoxydiphenylmethane (1) itself, the simplest compound of the series. It was shown using deuterium and ''C labelled 2methoxydiphenylmethanes (2, 3) that in this instance benzyl or tropilium ions are also formed through two alternative fragmentation routes.

📜 SIMILAR VOLUMES

Hydrogen-carbon, carbon-carbon double re
Hydrogen-carbon, carbon-carbon double rearrangement induced by proximity effects. 1–formation of methoxybenzyl ions in the electron impact mass spectra of substituted 1,1-bis(dimethoxyphenyl)methanes
✍ Leopoldo Ceraulo; Maria Concetta Natoli; Pasquale Agozzino; Mirella Ferrugia; Li 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 348 KB

The 75 eV electron impact mass spectra of 1,l-bis(dimethoxypheny1)methanes bearing u-methoxy groups are dominated by intense peaks corresponding, at least formally, to benzyl ions [ (CH,0)IC6H,CH, I + ( 6 ) . They arise from ions [ ((CH,O),C,H,),CHI + (u), which are in turn formed from molecular ion