The Wittig Synthesis. I. Use of Certain Aliphatic Aldehydes As Intermediates in the Synthesis of Olefins¹

Stereoselective Syntheses of the Isomeric 5, 10‐Pentadecadienals

“…The overall yield of (E)-10-pentadecen-5-yn-1-01 (26) from 16 with respect to (Z)-10-pentadecen-5-yn-1-01 (22) is unsatisfactory, but the reaction conditions have not yet been optimized. Lithium aluminium hydride reduction of 22 gave a 91% yield of (E,Z)-5,1O-pentadecadien-l-o1 (23) and catalytic hydrogenation of 26 quantitatively furnished the stereoisomeric (Z, E)-5,10-pentadecadien-l-o1 (27).…”

Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid

“…Likewise, the Wittig reaction of 9 with C 9 -phos-phorane, generated from 11 [16] gave 13 with 98% isomeric purity (by capillary GLC analysis) whose exclusive (Z)-geometry was also confirmed by 13 C NMR analysis as above. Its alkaline hydrolysis afforded the acid 2.…”

“…Acidic deprotection of 7 led to the hydroxy compound 8 with concomitant esterification. Its oxidation followed by a second Wittig reaction of the resultant aldehyde 9 with the C 7 -phosphorane, generated from 10 [13] under the above condition afforded the ester 12 with 97% isomeric purity (by capillary GLC analysis). This was converted to 1 by alkaline hydrolysis.…”

Acute Toxicity to the Golden Apple Snail and Estimated Bioconcentration Potential of Triphenylphosphine Oxide and Series of Related Compounds

“…Triphenylphosphine oxide is a major byproduct of the Wittig reaction, which is widely used in the synthesis of insect sex pheromones (Anderson and Henrick 1975;Henrick 1977;Lo et al 1988), and in the synthesis of olefins (Hauser et al 1963). The conventional Wittig reaction entails the reaction of a phosphonium ylide with an aldehyde or a ketone.…”