
TY  - JOUR
A1  - Crow, WD 
A1  - McNab, H 
A1  - Philip, JM 
T1  - Iminyl radicals in gas-phase synthesis. III. Synthesis of a terminally unsaturated nitrile
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 10
SP  - 2299
EP  - 2306
KW  - 
UR  - https://doi.org/10.1071/CH9762299 
N2  - 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. 
ER  -

