Collect. Czech. Chem. Commun. 1988, 53, 1287-1296

Uv-light- and radiation-initiated addition of acetaldehyde to allyl alkanoates

František Liškaa, Miroslav Valentaa, Jiří Fikara, Martina Jandováa, Miroslav Pešekb and Petr Trškaa

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
b Institute for Research, Production and Application of Radioisotopes, 102 27 Prague 10


UV-light- and γ-60Co-initiated addition of acetaldehyde to allyl formate (I) and allyl acetate (II) yielded the 1:1 adducts - 4-oxopentyl formate (III) and 4-oxopentyl acetate (IV), respectively, together with the 1:2 telomers - 7-formyloxy-4-formyloxymethyl-2-heptanone (V) and 7-acetoxy-4-acetoxymethyl-2-heptanone (VI). The initial radiation yields are: G(III) = 200·8, G(IV) = 211·3, G(V) = 39·5, G(VI) = 37·9. Base-catalyzed transesterification of oxopentyl alkanoates III and IV afforded 5-hydroxy-2-pentanone (XIV), the same reaction of dialkylalkanoates VI and VII gave 5-hydroxy-4-hydroxymethyl-2-heptanone (XV).