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Ion cyclotron resonance studies of alkylsilyl ions: V—The reactions of alcohols and ethers with the allyldimethylsilyl cation
Author(s) -
Blair Ian A.,
Trenerry V. Craige,
Bowie John H.
Publication year - 1980
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210150107
Subject(s) - chemistry , ion , yield (engineering) , adduct , ion cyclotron resonance , hydrogen , fourier transform ion cyclotron resonance , resonance (particle physics) , analytical chemistry (journal) , medicinal chemistry , cyclotron , atomic physics , organic chemistry , physics , thermodynamics
Diallyldimethylsilane provides a source of the allyldimethylsilyl cation in the ion cyclotron resonance spectrometer; reaction of this cation with alcohols (ROH) produces adducts which decompose by loss of C 3 H 6 to yield the ion \documentclass{article}\pagestyle{empty}\begin{document}$ \left[{{\rm Me}_2 \mathop {\rm S}\limits^{\rm + } {\rm i} - {\rm OR}} \right] $\end{document} . This elimination is thought to occur by a 1,5‐hydrogen shift, together with either stepwise or concerted silicon‐carbon bond cleavage. The corresponding aducts from ethers ROR 1 (R 1 ⩾R, R 1 ⩾Et) first lose (R 1 H˙) and then undergo the elimination described above.