Syntheses of tetra‐ and hexadeuterated octadecenoates

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Abstract
A study of the metabolism in man ofcis andtrans monoenoic acids required the synthesis of tetra- and hexadeutero-9-octadecenoates. Preparation of methyl 9-octadecenoate-8,8,11,11-d 4 (90 mol % deuterium) by the Wittig reaction was accompanied by deuterium scattering with sodium methoxide as the base but not with alkyllithium. Scattering occurred in both the aldehyde and phosphorane moieties only when the aldehyde contained deuterium on the alpha carbon. Methyl 9-octadecenoate-8,8,13,13,14-14-d 6 (98 mol % deuterium) was also prepared by the Wittig reaction. The deuterated octadecenoates were formed principally ascis isomers. Thetrans isomers were produced by nitrogen oxide isomerization and separation on a silver ion column.