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Structure elucidation of the intermediate in triethylborane‐mediated radical addition of oxime ethers with 2D‐ and 3D‐DOSY NMR
Author(s) -
Nakakoshi Masamichi,
Ueda Masafumi,
Sakurai Satoshi,
Miyata Okiko,
Sugiura Makiko,
Naito Takeaki
Publication year - 2006
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1847
Subject(s) - chemistry , triethylborane , oxime , ether , reaction intermediate , nuclear magnetic resonance spectroscopy , proton nmr , computational chemistry , medicinal chemistry , organic chemistry , catalysis
The structures of the components in the triethylborane‐mediated radical addition reaction of oxime ether were investigated by 1 H‐ and 3D‐DOSY NMR methods. It has been impossible to physically separate the unstable intermediates; therefore, the structures were thus far unidentified. It has been possible to elucidate the structures of these unstable intermediates using Diffusion‐Ordered Spectroscopy (DOSY) methods for the reaction in an NMR tube. The DOSY methods resolved the spectra of each starting compound, intermediate and product having different diffusion coefficients. The structure of the intermediate was shown to be due to the bonding of diethylborane to the nitrogen atom of the alkoxyamino group. Copyright © 2006 John Wiley & Sons, Ltd.