Action of Lithium Aluminum Hydride on Acetylenic Acids

Synthesis of Perdeuterated 1‐Palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phosphocholine ([D82]POPC) and Characterisation of Its Lipid Bilayer Membrane Structure by Neutron Reflectometry

“…Next, we applied the Sharpless method of asymmetric dihydroxylation to O‐benzyl‐protected deuterated allyl alcohol . Deuterated allyl alcohol was synthesised from propiolic acid (Scheme ), which was reduced with 25 % molar excess of lithium aluminium deuteride at room temperature by following the procedure reported by Benedict and Russell (which utilises LiAlH 4 ) . This reaction resulted in the formation of a mixture of [D 5 ]allyl alcohol and [D 7 ] n ‐propanol, which was used without further purification because it was anticipated that separation would be easier after the dihydroxylation step.…”

Emploi du bromure de vinylmagnésium pour la synthèse de molécules marquées au 14C: Nouvelle méthode de préparation de glycérol 14C‐1 et d'acide glycérique 14C‐1

“…L'hydroxylation de l'alcool allylique en glycCrol obtenue A I'aide de divers rtactifs [7,8,91 ne devait pas prisenter de difficult&. BENEDICT et RUSSELL [6] ont publie la reduction de l'acide acrylique en alcool allylique avec un rendement de 68 %, en employant un excbs de 40 74 de LiAIH,. Nous avons ttudit en dCtail cette rCduction.…”

“…un mClange d'acide propionique et d'acide acrylique dans la m&me proportion que les alcools. Ces rtsultats nous permettent de douter que [I71 ait pu obtenir de l'alcool allylique 14C-l pur en utilisant la mtthode de BENEDICT et RUSSELL [6].…”

Preparation of Novel Dideuterioallyl Mercaptan

“…3 The reference that was cited for the statement reported the reduction of acetylenedicarboxylic acid to 2-butene-1,4-diol (84% yield with 98% purity), fumaric acid to 2-butene-1,4diol (78% yield), acrylic acid (1) to allyl alcohol (2, 68% yield), and propiolic acid (5) to allyl alcohol (2, 85% yield). 4 Allyl alcohol (2) was not reduced to n-propyl alcohol (3) under the conditions, but such reduction was accomplished in 26% yield by heating the mixture in dibutyl ether at 100 o C for 3 h. 5 It should be pointed out that 0.75 mole of LiAlH 4 is required for reduction of 1 mole of RCOOH to RCH 2 OH and H 2 . But 0.283 mole of 1 and 0.35 mole of LiAlH 4 in ether was reacted at room temperature for 16 h for the reduction of 1 to 2.…”

“…But 0.283 mole of 1 and 0.35 mole of LiAlH 4 in ether was reacted at room temperature for 16 h for the reduction of 1 to 2. 4 Therefore, we attempted the reduction of acrylic acid (1) with LiAlH 4 to establish the suitable reaction conditions which would be adapted for the reduction with LiAlD 4 .…”