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Published 1986 | public
Journal Article

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

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.

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.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023