A one-pot preparation of allylsilanes and (Z)-alk-2-enyl silanes

Metalation of 1-alkenes with a mixt. of BuLi and KOCMe3 in tetrahydropyran, followed by stereochem. equilibration and treatment with Me3SiCl, afforded (2-alkenyl)trimethylsilanes in good yield and with Z:E ratios of 95:5 to 98:2. E.g., reaction of RCH2CH:CH2 (R = Pr, Bu, pentyl, hexyl, heptyl, octyl, nonyl) as above gave 52-75% Z-RCH:CHCH2SiMe3. Deprotonation of propene was rapidly and readily accomplished with a stoichiometric amt. of the superbase suspended in pentane on a 1 mol scale. [on SciFinder (R)]


Published in:
Synthesis, 2, 150-152
Year:
1997
Keywords:
Note:
CAN 126:157544
29-6
Organometallic and Organometalloidal Compounds
Institut Chimie Organique,Universite Lausanne,Lausanne-Dorigny,Switz.
Journal
0039-7881
written in English.
115-07-1 (1-Propene); 994-30-9 (Chlorotriethylsilane); 18162-48-6 (tert-Butyl(chloro)dimethylsilane); 58479-61-1 (tert-Butyl(chloro)diphenylsilane) Role: RCT (Reactant), RACT (Reactant or reagent) (one-pot synthesis of allylsilanes); 17898-21-4P (Allyltriethylsilane); 74472-22-3P (Allyl(tert-butyl)dimethylsilane); 138566-91-3P (Allyl(tert-butyl)diphenylsilane) Role: SPN (Synthetic preparation), PREP (Preparation) (one-pot synthesis of allylsilanes); 75-77-4 (Chlorotrimethylsilane); 111-66-0 (1-Octene); 112-41-4 (1-Dodecene); 124-11-8 (1-Nonene); 592-41-6 (1-Hexene); 592-76-7 (1-Heptene); 821-95-4 (1-Undecene); 872-05-9 (1-Decene) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective synthesis of alkenylsilanes); 63922-75-8P; 74676-14-5P; 91118-74-0P; 91899-36-4P; 117184-63-1P; 135457-22-6P; 187034-76-0P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective synthesis of alkenylsilanes)
Laboratories:




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


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