The synthesis of 3,4-2H2-3Z-Hexenal and 6,6,62H3-3Z-Hexenal

Article abstract of DOI:10.1002/jlcr.2580360510

6,6,6-²H₃-3Z-Hexenal (3b) has been prepared in 89% yield and in greater than 94% purity by the oxidation of 6,6,6³H₃-3Z-Hexen-1-of (2b) with the Dess/Martin periodinane (1) in fluorotrichloromethane (freon 11). Use of the freon solvent greatly improved the recovery of this volatile aldehyde. Similarly the oxidation of 3,4-²H₂-3Z-hexen-1-of (5) yielded 3,4-²H₂-3Z-hexenal (6) in a 92% isolated yield with a purity of greater than 99%. 3,4-²H₂-3Z-Hexen-1-of (5) Was prepared in 87% by the catalytic deuterogenation of 3-hexyn-1-of (4) in an improved synthetic procedure,