S. Fielder et Dd. Rowan, THE SYNTHESIS OF 3,4-H-2(2)-3Z-HEXENAL AND 6,6,6-H-2(3)-3Z-HEXENAL, Journal of labelled compounds & radiopharmaceuticals, 36(5), 1995, pp. 465-470
6,6,6-H-2(3)-3Z-Hexenal (3b) has been prepared in 89% yield and in gre
ater than 94% purity by the oxidation of 6,6,6-H-2(3)-3Z-Hexen-1-ol (2
b) with the Dess/Martin periodinane (1) in fluorotrichloromethane (fre
on 11), Use of the freon solvent greatly improved the recovery of this
volatile aldehyde, Similarly the oxidation of 3,4-H-2(2)-3Z-hexen-1-o
l (5) yielded 3,4-H-2(2)-3Z-hexenal (6) in a 92% isolated yield with a
purity of greater than 99%. 3,4-H-2(2)-3Z-Hexen-1-ol (5) was prepared
in 87% by the catalytic deuterogenation of 3-hexyn-1-ol (4) in an imp
roved synthetic procedure.