The preparation of N-cyanoammonium salts

✍ Scribed by Joesph V. Paukstelis; Moon-geu Kim

• Book ID: 104222571
• Publisher: Elsevier Science
• Year: 1970
• Tongue: French
• Weight: 169 KB
• Volume: 11
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89380-6

✦ Synopsis

N-Cyanotrialkylammonium salts have been previously postulated only as reactive intermediates in the von Braun cyanogen bromide reaction (2-4). The reaction is presumed to proceed by formation of the NLcyanotrialkylammonium ion which in a subsequent but rapid step is attacked by the counter ion, bromide, to give a cyanamine and an alkyl bromide (4). If the second step could be prevented by exchange of the counter ion for one that is a less potent nucleophile then the intermediate N-cyanotrialkylammonium salt might be sufficiently stable for isolation.

We wish to report that we have isolated several N-cyanotrialkylammonium fluroborates and