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Direct observation of the unstable intermediates in radical addition reaction by using an interfacing microchip combined with an NMR
Author(s) -
Nakakoshi Masamichi,
Ueda Masafumi,
Sakurai Satoshi,
Asakura K.,
Utsumi Hiroshi,
Miyata Okiko,
Naito Takeaki,
Takahashi Yutaka
Publication year - 2007
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.2087
Subject(s) - chemistry , interfacing , nuclear magnetic resonance spectroscopy , fluorine 19 nmr , triethylborane , reaction intermediate , anhydrous , proton nmr , radical cyclization , analytical chemistry (journal) , organic chemistry , political science , law , catalysis
Direct observation of the unstable intermediate in the radical addition reaction of the oxime ether 1 mediated by triethylborane (Et 3 B) is described using 1 H and 11 B micro channeled cell for synthesis monitoring (MICCS), which was recently developed as an interfacing microchip for NMR. It was possible that the signal of the intermediate was observed as a result of using MICCS technique with a standard NMR instrument. This result supports the structure of the intermediate analyzed by diffusion‐ordered spectroscopy (DOSY) NMR method in a previous paper. The procedure of micro channeled cell for synthesis monitoring‐nuclear magnetic resonance (MICCS‐NMR) was much easier than that of DOSY method. It was proven that it could be applied to the reaction in an anhydrous condition. Copyright © 2007 John Wiley & Sons, Ltd.