1.1: 88 percent / NaH / dimethylformamide / 6.5 h / 20 °C 2.1: O3 / methanol / -78 °C 2.2: Me2S; p-CH3C6H4SO3H / methanol / -78 - 20 °C 2.3: 98 percent / amberlyst-15 / acetone / 20 °C 3.1: 97 percent / H2 / Pd/C / methanol / 25 °C / 3040 Torr View Scheme

in tetrahydrofuran byproducts: Mn2(CO)10; KMn(CO)5 in THF was added dropwise to stirred soln. of allyl halide (3-fold excess) in THF under N2;; evapd. in vac., addn. of pentane, filtered through Celite, cooled to -78 °C, crystals of Mn(CO)5Br were syringed off; approx. 90percent purity, contaminated;;

N-bromosuccinmide in tetrachloromethane HeatingIrradiation;

phosphorus tribromide in diethyl ether T=0 - 20°C; Inert atmosphere;

(i) I2, (ii) NBS, (PhCO)2O2, CCl4; Multistep reaction;

1: sodium tetrahydroborate / diethyl ether; methanol / 0 - 20 °C / |Inert atmosphere 2: phosphorus tribromide / diethyl ether / 0 - 20 °C / |Inert atmosphere View Scheme

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 8 h; Heating; Yield given. Yields of byproduct given;

potassium carbonate in acetone

(i) Ag2CO3-celite, (ii) /BRN= 635752/; Multistep reaction;