Structural Characterization of N-Protonated Amides. Regioselective N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactams

View/ Open
Issue Date
2010-07-07Author
Szostak, Michal
Yao, Lei
Day, Victor W.
Powell, Douglas R.
Aubé, Jeffrey
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Metadata
Show full item recordAbstract
The straightforward protonation of lactams by treatment with acid and the full structural characterization of three resulting N-protonated lactams are disclosed. This work provides experimental evidence that N-protonation of amide bonds results in a dramatic increase of non-planarity about the C-N amide bond. The resulting compounds are discussed in structural, spectroscopic, and reactivity terms. The data suggests that ca. 50° distortion of these amide bonds suffices for their efficient N-activation.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/ja101690u.
Collections
Citation
Szostak, M., Yao, L., Day, V. W., Powell, D. R., & Aubé, J. (2010). Structural Characterization of N-Protonated Amides. Regioselective N-Activation of Medium-Bridged Twisted Lactams. Journal of the American Chemical Society, 132(26), 8836–8837. http://doi.org/10.1021/ja101690u
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.