Metalated phenylphosphine oxides reacted with aldehydes at room temp. to give trans olefins with high selectivity. Thus, Ph2P(O)CH2Ph was treated with BuLi, then with PhCHO to give 78% trans-stilbene. The configuration of a double bond present in the starting material was conserved throughout the reaction sequence, e.g., (E)-Ph2P(O)CH:CHMe reacted with BuLi and PrCHO to give 28% (E,E)-MeCH:CHCH:CHPr, with only traces of the other isomers. [on SciFinder (R)]
Titre
Die Horner-Variante der Wittig-Reaktion : unter milden Bedingungen durchführbar und mit stereochemischen Optionen ausgestattet
Publié dans
Chimia
Volume
30
Numéro
3
Pages
197-9
Date
1976
ISSN
0009-4293
Note
CAN 85:176734
23-2
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in German.
2959-74-2; 17668-60-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with aldehydes); 1733-57-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with benzaldehyde, stereoselective); 103-30-0P; 873-66-5P; 60919-80-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by Wittig reaction, stereoselective); 123-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with diphenylbutenylphosphine oxide); 100-52-7 Role: RCT (Reactant), RACT (Reactant or reagent) (with diphenylbenzylphosphine oxide)
Date de création de la notice
2006-03-03
