Keese, Reinhart; Berdat, Francois; Macchi, Piero (2013). Stereoselectivity of Additions to N-Methyl Acetonitrilium Fluorosulfonate. Journal of organic chemistry, 78(5), pp. 1965-1970. American Chemical Society 10.1021/jo301983s
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Alkoxy-N-methyl-acetiminium salts were prepared by addition of CH3OH and C2H5OH to N-methyl acetonitrilium fluorosulfonate at low temperature. Analysis of the (5)J(HH) and (3)J(13)C-H coupling constants in the NMR spectra showed an anti addition with a diastereoselectivity of >9596. Deprotonation of these salts with (Z)-configuration gave the corresponding N-methyl-alkoxyacetimines with very high (E)-configuration. Upon protonation at -78 degrees C, these iminoesters gave the corresponding alkoxy-N-methyl-acetirninium salts with (E)-configuration. Computational analyses of the iminoesters and the corresponding iminium cations including the conformations give insight into the relative stability. Nitrilium salts can be used as reagents, exemplified by some esterifications between simple acids and alcohols.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Other Institutions > Emeriti, Faculty of Science 08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Keese, Reinhart, Macchi, Piero |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
0022-3263 |
Publisher: |
American Chemical Society |
Language: |
English |
Submitter: |
Piero Macchi |
Date Deposited: |
10 Apr 2014 15:12 |
Last Modified: |
05 Dec 2022 14:30 |
Publisher DOI: |
10.1021/jo301983s |
BORIS DOI: |
10.7892/boris.45661 |
URI: |
https://boris.unibe.ch/id/eprint/45661 |
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