91890-74-3Relevant academic research and scientific papers
Synthesis of mono- and 1,3-disubstituted allenes from propargylic amines via palladium-catalysed hydride-transfer reaction
Nakamura, Hiroyuki,Ishikura, Makoto,Sugiishi, Tsuyuka,Kamakura, Takaya,Biellmann, Jean-Francois
experimental part, p. 1471 - 1477 (2008/10/09)
Mono- and 1,3-disubstituted allenes were synthesized from the corresponding propargylamines via palladium-catalysed hydride-transfer reaction. In the current transformation, propargylic amines can be handled as allenyl anion equivalents and introduced int
Selenylated dienes: synthesis, stereochemical studies by 77Se NMR, and transformation into functionalized allenes
Redon, Sebastien,Berthe Berkaoui, Anne-Lise,Pannecoucke, Xavier,Outurquin, Francis
, p. 3707 - 3717 (2007/10/03)
2-Phenylselanyl-1,3-dienes 3-8 were prepared by a Wittig or Wittig-Horner-Emmons procedure starting from α-phenylselanyl α,β-unsaturated aldehydes. Ratio and configuration of each diene isomers were determined by 77Se and 1H NMR. The
Syntheses d'alcools allyliques et alleniques fonctionnels a partir de composes carbonyles α-phenylselenies
Lerouge, Patrice,Paulmier, Claude
, p. 1225 - 1229 (2007/10/02)
The functionalized allylic selenides 6, 7, 8, 10 and 11 were prepared from phenylselenoaldehydes and ketones 1, and phenylselenopyruvates 2 using the Wittig or the Horner reaction. 2,3-Sigmatropic rearrangement of the corresponding selenoxides leads to the functional allylic alcohols 15, 16 and 17 and to the conjugated enals 18, 19 and 20.A method for the conversion of an aldehyde into the enal with an additional carbon is described.The functional 3-phenylselenobutadienes 23, 24 and 25 were also obtained from α-phenylselenoenals 21 in the same manner.An oxidation-rearrangement reaction appears to be a convenient way to prepare the functional or substitued allenic alcohols 26 and 28.The ethyl 2-hydroxy pent-3,4-dienoate 26c has been cyclized by benzeneselenenyl bromide into the ethyl 2,5-dihydrofurancarboxylate 29.
SYNTHESE D'α-HYDROXYALLENES α-FONCTIONNALISES A PARTIR D'α-PHENYLSELENOENALS
Lerouge, Patrice,Paulmier, Claude
, p. 1987 - 1990 (2007/10/02)
Morpholinobenzeneselenenamide (MBSe) react with enals to form α-phenylselenoenals which undergo Wittig and Horner reactions.We synthetise 1-substituted 3-phenylseleno-1,3-butadienes.Oxidation and subsequent 2,3-sigmatropic rearrangement lead to α-fonctionnalized α-hydroxyallenes.This compounds give access to 2,5 dihydrofurans.
