A synthetic method for direct conversion of ketones into cyanides. Introduction of a one carbon unit.

✍ Scribed by O.H. Oldenziel; A.M. van Leusen

• Book ID: 104246874
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 188 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95942-8

✦ Synopsis

The usefulness of tosylmethylisocyanid (To&K) in the synthesis of several azoles has been shown in a recent series of papers, 2 Two different types of product have been obtained thus far by reaction of TosMIC (I) with ketones 3,4 , see Scheme [l]. It also has been shown that tosyl-(*~ + -(:'i.:l;) ] TosCH N=C R' 'Tos (III) substituted 2-oxazolines (II) are intermediates in the formation of III. 4 El1 Recently,we reported a seeming exceptim to Scheme [II, in that adamantanane was converted to 2-cyanoadamantane. 5 0 + TosCH2N=C NaOEt, O°C (I) DME, EtOH

PI

We now wish to report the extension of this reaction into a general synthetic method for the conversion of ketcmes to cyanides. Furthermore, as in Scheme [l], tosyl-substituted oxazolines