The preparation of pure allyl- and benzyl-type organoalkali intermediates via organotin compounds
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)]
1991
409
1-2
93
101
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)
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