The preparation of pure allyl- and benzyl-type organoalkali intermediates via organotin compounds
Desponds, Olivier; Schlosser, Manfred
1991

Abstract

Superbase metalation of alkenes or alkylbenzenes and subsequent condensation with trialkylstannyl chloride affords allyl- or benzyl-type organotin compds. that can be isolated in pure form. Treatment with sol. reagents such as methyllithium, trimethylsilylmethylpotassium and trimethylsilylmethylcesium generates the corresponding organoalkali derivs., almost quant. and in high purity, suitable for kinetic or spectroscopic studies. E.g., treating Me3SiC(:CH2)Me with KOCMe3 and BuLi in THF and then with Me3SnCl gave 45% CH2:C(SiMe3)CH2SnMe3, which when treated with Me3SiCH2Cs gave 95% of the Cs deriv. [on SciFinder (R)]

Details

Title The preparation of pure allyl- and benzyl-type organoalkali intermediates via organotin compounds
Author(s) Desponds, Olivier ; Schlosser, Manfred
Published in Journal of Organometallic Chemistry
Volume 409
Issue 1-2
Pages 93-101
Date 1991
Keywords
Note CAN 115:92443 29-8 Organometallic and Organometalloidal Compounds Inst. Chem. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0022-328X written in English. 98-83-9; 115-07-1 (1-Propene); 115-11-7; 590-18-1 (cis-2-Butene); 1647-16-1 (1,9-Decadiene); 4900-30-5 (1,8-Nonadiene); 18163-07-0; 22364-43-8; 102871-32-9 Role: RCT (Reactant), RACT (Reactant or reagent) (deprotonation and metalation of, organostannane by); 766-04-1P; 3052-45-7P; 19104-13-3P; 59304-72-2P; 63226-59-5P; 64544-47-4P; 135387-09-6P; 135387-10-9P; 135387-11-0P; 135387-12-1P; 135387-13-2P; 135387-14-3P; 135387-15-4P; 135387-16-5P; 135387-17-6P; 135387-18-7P; 135419-01-1P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, by transmetalation of organostannane); 1066-45-1 (Trimethylchlorostannane) Role: RCT (Reactant), RACT (Reactant or reagent) (metalation with, of deprotonated alkenes or alkylbenzenes); 762-73-2P; 16327-46-1P; 28493-54-1P; 35998-94-8P; 55562-82-8P; 135387-00-7P; 135387-01-8P; 135387-02-9P; 135387-03-0P; 135387-04-1P; 135387-05-2P; 135387-06-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and transmetalation of, with organoalkali reagents); 3200-73-5P; 37506-25-5P; 76505-19-6P; 135387-07-4P; 135387-08-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 6088-87-5 Role: RCT (Reactant), RACT (Reactant or reagent) (transmetalation of, organostannane by); 53127-82-5; 53127-84-7 Role: RCT (Reactant), RACT (Reactant or reagent) (transmetalation with, of organostannanes)
DOI https://doi.org/10.1016/0022-328X(91)86134-C
Laboratories LSCO
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2006-03-03