
%0 Journal Article
%A Crow, WD 
%A McNab, H 
%A Philip, JM 
%T Iminyl radicals in gas-phase synthesis. III. Synthesis of a terminally unsaturated nitrile
%J Australian Journal of Chemistry
%D 1976/10/01
%V 29
%N 10
%P 2299-2306
%K 
%R https://doi.org/10.1071/CH9762299
%U https://www.publish.csiro.au/paper/CH9762299 
%X The previously reported generation of &#945;- and &#969;-cyanoalkyl radicals has been substantially improved by the use of the oxime esters of cyclopentanone and cyclohexanone instead of the azines. Fragmentationof the &#945;-cyanoalkyl radicals to acrylonitrile is still observed, but the efficiency of alkylation of the residue is considerably enhanced. A synthetic device is described for intercepting the first-formed&#969;-cyanoalkyl radicals with the formation of terminally unsaturated nitriles. This involves pyrolysis of the 5,6-dihydro-4H-l,2-oxazin-6-ones. The preparation and pyrolysis of 4,4a,5,6-tetrahydro-3H-naphth[l,2-c][1,2]oxazin-3-one to 2-(but-3-eny1)benzonitrile is described. 
