SCOOPY-Reaktionen : Die Regioselektivität der Alkenol-Synthese

Ph3P+CH2R (R = H, Me) reacted with aldehydes R1CHO (R1 = n-C5H11, Me2PrC, Ph) in the presence of BuLi and HCHO to give primary alkenols R1CH:CRCH2OH; ketones R2R3CO [R2, R3 = Me, Ph or (CH2)4, (CH2)5] and spatially crowded aldehydes gave secondary and tertiary alcs. R2R3C(OH)CR:CH2. A b-oxido phosphonium ylide was a reaction intermediate. [on SciFinder (R)]


Published in:
Synthesis, 10, 575-6
Year:
1972
Keywords:
Note:
CAN 78:57668
23-7
Aliphatic Compounds
Org.-Chem. Inst.,Univ. Heidelberg,Heidelberg,Fed. Rep. Ger.
Journal
0039-7881
written in German.
115-18-4P; 931-43-1P; 932-89-8P; 1940-19-8P; 3859-35-6P; 4383-08-8P; 4393-06-0P; 4407-36-7P; 18409-17-1P; 26001-58-1P; 33965-54-7P; 39924-61-3P; 39924-62-4P; 39924-63-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 66-25-1; 120-92-3; 14250-88-5 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with alkyltriphenylphosphonium bromide in presence of butyllithium and formaldehyde); 1530-32-1; 1779-49-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with carbonyl compds. in presence of butyllithium and formaldehyde); 50-00-0 Role: RCT (Reactant), RACT (Reactant or reagent) (with alkyltriphenylphosphonium bromide and carbonyl compds. in presence of butyllithium); 109-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (with alkyltriphenylphosphonium bromide and carbonyl compds. in presence of formaldehyde); 67-64-1; 98-86-2; 100-52-7; 108-94-1 Role: RCT (Reactant), RACT (Reactant or reagent) (with alkyltriphenylphosphonium bromide in presence of butyllithium and formaldehyde)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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