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Synthesis, spectroscopy and polymerization of methyl α-([13C,15N]isocyano)propionate; acetic formic anhydride as N-formylating reagent

✍ Scribed by Edward J. Vlietstra; Roeland J. M. Nolte; Jan W. Zwikker; Wiendelt Drenth; Richard H. A. M. Jansen


Book ID
104588425
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
567 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

Methyl α‐([^13^C,^15^N]isocyano)propionate was prepared starting from (±)‐[^15^N]alanine. The amino acid was converted into the methyl ester, which was formylated with acetic [^13^C]‐formic anhydride, to afford the methyl ester of N‐[^13^C]formyl[^15^N]alanine. Dehydration of the latter compound gave the isocyanide, which was polymerized with nickel chloride. ^1^H, ^13^C, ^15^N NMR and IR data of the labelled compounds are presented.