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A ^(15)N NMR Study of the Ring-Opening of Methylsydnonimine Hydrochloride

Roberts, John D. and Stefaniak, Lech and Webb, Graham A. and Witanowski, Michal (1986) A ^(15)N NMR Study of the Ring-Opening of Methylsydnonimine Hydrochloride. Bulletin of the Polish Academy of Sciences Chemistry, 34 (3-4). pp. 81-88. ISSN 0001-4095. http://resolver.caltech.edu/CaltechAUTHORS:20151103-070435473

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Abstract

Nitrogen-15 NMR spectroscopy has been used to study the irreversible ring-cleavage or 3-methylsydnonimine hydrochloride samples separately labeled with ^(15)N at each or the three possible nitrogens. This reaction, which occurs in hydroxylic solvents on addition of base, initially yields principally the E and Z isomers or N-methyl-N-cyanomethylnitrosamine. While 3-methylsydnonimine itselr is surely a transient intermediate in the ring-opening, no measurable concentration of the free base could be detected by ^(15)N NMR. Hydrolysis or the cyano group of N-methyl-N-cyanomethylnitrosamine to give E and Z isomers of N-methyl-N-nitrosoglycine amide and N-methyl-N-nitrosoglycine could also be followed by ^(15)N NMR and is reasonably facile in that it occurs significantly at below room temperature.


Item Type:Article
Additional Information:© 1986 Polish Academy of Sciences. This research was supported in part by the National Science Foundation and by the Polish Academy of Sciences, Grant MR-I.9.2.
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Funding AgencyGrant Number
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Polish Academy of SciencesMR-I.9.2
Record Number:CaltechAUTHORS:20151103-070435473
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151103-070435473
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61778
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Nov 2015 21:28
Last Modified:04 Nov 2015 21:28

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