SCOOPY and oxirane reactions: a-lithio-ylides vs. conventional ylides
Ph3P:CH2 reacted with epoxides I (R = H, Me, vinyl; R1 = H, Me) or cyclohexene oxide in the presence of 1.2 equiv LiX (X = Br, iodo, BPh4) to give Ph3P+CH2CH2CRR1OH X- or 83% trans-II. Similarly, Ph3P:CH, I (R = R1 = H) and LiBr gave 68% Ph3P+CHMeCH2CH2OHBr-. Thus it is unnecessary to use a-lithio-ylides. [on SciFinder (R)]
1983
37
1
10
11
CAN 98:198358
29-7
Organometallic and Organometalloidal Compounds
Inst. Chim. Organ.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
51860-45-8P; 85769-75-1P; 85769-76-2P; 85769-78-4P; 85769-81-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by reaction of epoxide and methylene triphenylphosphorane, in presence of lithium salt); 85769-79-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by reaction of ethylene oxide and ethylene triphenylphosphorane, in presence of lithium salt); 3487-44-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with epoxides, in presence of lithium salts); 1754-88-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with ethylene oxide, in presence of lithium salts); 75-21-8; 75-56-9; 286-20-4; 558-30-5; 1838-94-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with methylene triphenylphosphorane, in presence of lithium salt)
REVIEWED
EPFL