54364-61-3Relevant academic research and scientific papers
THE WITTIG REACTION: COMMENTS ON THE MECHANISM AND APPLICATION AS A TOOL IN THE SYNTHESIS OF CONJUGATED DIENES
Ideses, Rut,Shani, Arnon
, p. 3523 - 3534 (2007/10/02)
For construction, by the Wittig reaction, of conjugated dienes with specific stereochemistry (either Z or E) at the newly formed double bond, without isomerization of the existing ("old") double bond, it is better to react a reactive (nonstabilized) saturated ylide with an α,β-unsaturated aldehyde.The opposite approach, namely, the reaction of a moderate (semi-stabilized) allylic ylide with a saturated aldehyde produces a mixture of geometric isomers, as a result of increased production of the E-configuration at the new double bond, and significant isomerization of the existing double bond.The proposed betaine structure for the intermediate could account only for the two equivalents of Li reaction.In other reactions, the less stable erythro-oxaphosphetane is probably the intermediate, produced by an early anti- or gauche C-C bond formation from the ylide and the carbonyl, from which the Z-double bond is then formed.
Systematic Syntheses and Charactarization of Dodecadien-1-ols with Conjugated Double Bond, Lepidopterous Sex Pheromones
Ando, Tetsu,Kurotsu, Yuichi,Kaiva, Mieko,Uchiyama, Masaaki
, p. 141 - 148 (2007/10/02)
Four geometrical isomers of 5,7-, 6,8-, 7,9- and 8,10-dodecadein-1-ols were systematically synthesized by two routes.One involved the Wittig reaction between (E)-2-alkenal and a phosphorane with an appropriate carbon chain, and yielded a mixture of (E,Z)- and (E,E)-isomers in a ratio of ca. 3:2.The other route comprised of the Wittig reaction of a 2-alkynal and the stereoselective reduction of the triple bond to a (Z)-double bond via hydroboration with dicyclohexylborane to give a mixture of (Z,Z)- and (Z,E)-isomers in a ratio of 6:1 10:1.Both the mixtures were separately chromatographed on a silica gel column impregnated with silver nitrate to give four geometrically pure isomers.With 9,11-diene they were analysed by GC on a capillary column, HPLC, silver nitrate impregnated TLC, and 13C NMR.
STEREOSELECTIVE SYNTHESIS OF (E)-7, (Z)-9 DODECADIEN-1-YL ACETATE
Descoins, C.,Lettere, M.,Linsrumelle, G.,Michelot, D.,Ratovelomanana, V.
, p. 761 - 774 (2007/10/02)
Two convenient synthetic methods for (E)-7, (Z)-9 dodecadien-1-yl acetate, via palladium-copper catalysed reactions of acetylenic intermediates with vinylic halides, are presented.
