1: diethyl ether 2: CH3COCl 3: diethyl ether View Scheme

ammonium chloride; zinc in tetrahydrofuran; water Ph3SnCl is added to THF/H2O (NH4Cl saturated) mixt. with excess of zinc powder, appropriate allyl bromide is added dropwise under stirring within 5 min, filtn. after 1 h of mixing, THF is removed, residue is treated with chloroform; extn. (chloroform), drying (Na2SO4), solvent is evapd., treated with petroleum ether or n-hexane, solvent is evapd., crystd. (ethanol), mixt. of Ph3SnCHCCH2 and Ph3SnCH2CCH ratio 58:42; total yield 74percent;

1: HCl 2: diethyl ether View Scheme

2: I2 3: diethyl ether View Scheme

2,2'-azo-bisisobutyronitrile in benzene T=70°C; 8 h;

2: diethyl ether View Scheme

2: diethyl ether 4: Br2 / tetrachloromethane View Scheme

2: methanol 3: I2 View Scheme

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