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Anionic rearrangements of deprotonated α‐alkoxyvinyltrimethylsilanes in the gas phase
Author(s) -
Eichinger Peter C. H.,
Bowie John H.
Publication year - 1991
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290051213
Subject(s) - chemistry , deprotonation , gas phase , medicinal chemistry , ion , stereochemistry , phase (matter) , organic chemistry
α‐Alkoxyvinyltrimethylsilanes deprotonate to form two species − CHC(SiMe 3 )OR and CH 2 C(Si(Me) 2 CH 2 − )OR. The silylcarbanion undergoes the unusual rearrangement reaction CH 2 C(Si(Me 3 ) 2 CH 2 − )OR → ((CH 2 CO)Me 2 RSiCH 2 − ) Me 2 RSiCH 2 − + CH 2 CO. Loss of (R‐H) occurs when R ≥ Et; it is suggested that this is a reaction of the vinvl anion system.