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NMR, IR, and ESR spectroscopic investigation of reaction of α ‐silylamines with carbon tetrachloride
Author(s) -
Lazareva Nataliya F.,
Vakul'skaya Tamara I.,
Lazarev Igor M.
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1442
Subject(s) - chemistry , reactivity (psychology) , reagent , solvent , carbon tetrachloride , electron paramagnetic resonance , radical , photochemistry , medicinal chemistry , organic chemistry , nuclear magnetic resonance , physics , alternative medicine , pathology , medicine
This paper reports about high reactivity of α ‐silylamines in the reaction with CCl 4 . Unlike Et 3 N, α ‐silylamines rapidly react with CCl 4 upon irradiation with daylight to form α ‐silylamine hydrochloride salts in 92–98% yields. The influence of structure of α ‐silylamines and solvent on the degree of conversion was displayed. The interaction of α ‐silylamines with CCl 4 was studied by NMR, ESR, and IR spectroscopy. C‐centered radicals of α ‐silylamines were detected by ESR spectroscopy with spin traps (MNP, ND, and PBN) in reaction mixtures in CH 3 CN and C 6 H 6 and it show the radical character of this reaction. Both CH 3 CN and C 6 H 6 serve as solvents as well as reagents for this reaction. A mechanism of an interaction between α ‐silylamines and CCl 4 is discussed. Copyright © 2008 John Wiley & Sons, Ltd.