A-Isonitrosoketones

Indoles have been prepared from reactions of o-aminophenylketones with reactive , or stable " arsonium ylides. Oxo-stabilized ylides reacted with 2-chloro-oximes to give trans-5-acyl-A -isoxazolines, and isoxazoles have been obtained from reactive arsonium ylides and a-isonitrosoketones, and from triphenylarsonium methylide and nitrile oxides The latter ylide reacts similarly with nitrile imines to give pyrazoles. With triphenylarsonium benzylides and benzoylylides,benzene diazonium salts give 1,3,4,6-substituted 1,4-dihydro-1,2,4,5-tetrazines in a reaction in which initial coupling of the reagents is followed by a dimerisation. ... 

Via intermediates Phenols from hydrocarbons via amines s. 1,192 a-Hydroxy ketones from ketones via a-isonitrosoketones s. 2,145 a-Hydroxycarboxylic acids from carboxylic acids via a-halogenocarboxylic acids s. 1,451 v.l. H —OH... 

Startg. a-isonitrosoketone allowed to react with H2SO4 in moist acetic acid imide. Y 16%. E.R.H. Jones et al., Chem. Commun. 1968, 210. 

---