Ring tension, hydrocarbon acidity, and new super-bases
Addn. of di-Na pinacolate or KOCMe3 increased the transmetalating power of pentylsodium in alkane solvents. Some hydrocarbons thus metalated were Me3CCH:CH2, camphene, bicyclo[2.2.2]octene, spiro[4.4]nona-1,3-diene, nortricyclane, norcarane, and housane. Cyclobutanes remained inert. [on SciFinder (R)]
1986
40
9
306
308
CAN 107:59068
29-2
Organometallic and Organometalloidal Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
287-23-0 (Cyclobutane); 4755-33-3; 4806-58-0; 4806-59-1; 15358-91-5 (trans-Myrtanol) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted transmetalation of, by pentylsodium); 865-47-4; 109289-48-7 (Disodium pinacolate) Role: PRP (Properties) (effect of, on transmetalation of hydrocarbons by pentylsodium); 2716-23-6P; 2987-16-8P; 20107-37-3P; 31297-51-5P; 36744-59-9P; 40154-85-6P; 54382-52-4P; 57566-92-4P; 64081-43-2P; 109263-32-3P; 109263-33-4P; 109289-47-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 1822-71-5 (Pentylsodium) Role: RCT (Reactant), RACT (Reactant or reagent) (transmetalation by, of hydrocarbons, effect of activators on); 79-92-5 (Camphene); 185-94-4 (Housane); 279-19-6; 286-08-8; 558-37-2 (3,3-Dimethyl-1-butene); 766-29-0; 931-64-6 Role: RCT (Reactant), RACT (Reactant or reagent) (transmetalation of, by pentylsodium, effect of activators on)
REVIEWED
EPFL