C‐Nitroso compounds. Part XXXVI. Rearrangement of 2‐chloro‐2‐nitrosofenchane and 2‐chloro‐2‐nitrosocamphane

Abstract

Abstract2‐Chloro‐2‐nitrosofenchane 7 rearranges under the influence of aluminium chloride to the isomeric chloronitrones 9 and 12 (Scheme 3). 2‐Chloro‐2‐nitrosocamphane 18 (Scheme 4) gives, under similar conditions, only one chloronitrone 19, despite the close structural relationship between the starting materials 7 and 18. The chloronitrones react with all common nucleophiles, e.g. with water, to give hydroxamic acids, which can easily be reduced to the amides 4, 5 and 6. The first and last of these amides are not accessible by Beckmann rearrangement of the appropriate oximes.