trimethylsilyl bromide; 4 A molecular sieve in dichloromethane T=-30°C; 0.416667 h;

n-butyllithium in ethylene glycol dimethyl ether T=-78°C; 0.0333333 h;

n-butyl chloride in ethylene glycol dimethyl ether under argon; tin compound in DME cooled to -78 °C; nBuLi added; quench with excess alkyl halide;; poured in NH4Cl-soln./petroleum ether; sepn. of org. layer; dried; concd.; chromd.; NMR;

methanol in ethylene glycol dimethyl ether under argon; tin-compound in DME cooled to -78 °C; LiBu was added over 10 s; after 2 min solution was quenched with excess MeOH;; poured into NH4Cl-soln. and petroleum ether, shaked 1 min, organic layer sepd., washed (brine), dried (Na2SO4), filtered, concd. (vacuo); chromd. (silica gel; trace ethyl acetate/petroleum ether); (1)H- and (13)C-NMR; IR, MAS;;

n-butyl chloride in ethylene glycol dimethyl ether under argon; tin compound in DME cooled to -78 °C; LiBu added; quench with excess alkyl halide;; poured in NH4Cl-soln./petroleum ether; sepn. of org. layer; dried; concd.; chromd.; NMR;;

3-chloroprop-1-ene in ethylene glycol dimethyl ether under argon; tin compound in DME cooled to -78 °C; nBuLi added; quench with excess alkyl halide;; poured in NH4Cl-soln./petroleum ether; sepn. of org. layer; dried; concd.; chromd.; NMR;

N-ethyl-N,N-diisopropylamine in dichloromethane 18 h; Ambient temperature;

n-butyllithium; 1-iodo-butane Yield given. Multistep reaction;

n-butyllithium Yield given. Multistep reaction;

n-butyllithium Yield given. Multistep reaction;