The regioselectivity of 1,3-disubstituted allylmetal species towards electrophiles. 1-(Trimethylsilyl)alk-2-enylpotassium compounds

1-(Trimethylsilyl)alk-2-enylpotassium species are readily generated by deprotonation of (alk-2-enyl)trimethylsilanes with the superbasic mixt. of BuLi and KOCMe3. Like the parent compd., [1-(trimethylsilyl)allyl]potassium, they react with a variety of electrophiles preferentially, if not exclusively, at the silyl-distant terminus of the allyl moiety, thus producing branched ene silanes. The opposite regioselectivity previously obsd. with MeI hence appears to be an exception. [on SciFinder (R)]


Published in:
Synthesis, 5, 707-709
Year:
1998
Keywords:
Note:
CAN 129:41181
29-6
Organometallic and Organometalloidal Compounds
Institut Chimie Organique,Universite Lausanne,Lausanne,Switz.
Journal
0039-7881
written in English.
75-77-4; 100-52-7 (Benzaldehyde); 123-38-6 (Propanal); 762-72-1 (Allyltrimethylsilane); 40762-94-5; 74676-14-5; 91899-36-4; 117184-63-1; 152578-86-4 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselectivity in electrophilic substitution of allylsilanes); 52152-48-4P; 59376-64-6P; 84110-23-6P; 86936-05-2P; 87428-76-0P; 87428-78-2P; 208241-00-3P; 208241-01-4P; 208241-02-5P; 208241-03-6P; 208241-04-7P; 208241-05-8P; 208241-06-9P Role: SPN (Synthetic preparation), PREP (Preparation) (regioselectivity in electrophilic substitution of allylsilanes)
Laboratories:




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


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