Sulfates complex hydrides

The indol-3-yl-substituted indolo[2,3-()]carbazole 143 has been isolated as a product from the complex mixture generated by the decomposition of urorosein (144) (99CHE561). Interestingly, when subjected to alkylation conditions involving sodium hydride and dimethyl sulfate in THF, 143 was transformed into the N. -dimethyl derivative 145 in 36% yield (00MI2). 

To a stirred flask containing a suspension of 4.8 gm (0.2 mole) of sodium hydride in 50 ml of THF under a nitrogen atmosphere is added dropwise 13.3 gm (0.2 mole) of cyclopentadiene. In a separate flask are mixed 19.8 gm (0.2 mole) of A-methyl-2-pyrrolidone and 25.2 gm (0.2 mole) of dimethyl sulfate. (NOTE Separately A-methyl-2-pyrrolidone and dimethyl sulfate should be anhydrous and should be purified by distillation before reacting with each other to form the complex.) The latter mixture is heated for 20 min on a steam bath, cooled, and then added dropwise to the cyclopentadienylsodium solution at —5°C. After the addition, the reaction mixture is stirred for 2 hr, filtered, the filtrate concentrated, and the residue is obtained as a brown oil. On cooling, the brown oil solidifies and is recrystallized from cyclohexane to afford pale-yellow needles weighing 14.0 gm (50%), m.p. 100°-101°C. 

Arene(tricarbonyl)chromium complexes, 19 Nickel boride, 197 to trans-alkenes Chromium(II) sulfate, 84 of anhydrides to lactones Tetrachlorotris[bis(l,4-diphenyl-phosphine)butane]diruthenium, 288 of aromatic rings Palladium catalysts, 230 Raney nickel, 265 Sodium borohydride-1,3-Dicyano-benzene, 279 of aryl halides to arenes Palladium on carbon, 230 of benzyl ethers to alcohols Palladium catalysts, 230 of carboxylic acids to aldehydes Vilsmeier reagent, 341 of epoxides to alcohols Samarium(II) iodide, 270 Sodium hydride-Sodium /-amyloxide-Nickel(II) chloride, 281 Sodium hydride-Sodium /-amyloxide-Zinc chloride, 281 of esters to alcohols Sodium borohydride, 278 of imines and related compounds Arene(tricarbonyl)chromium complexes, 19... 

Metal cyanides(and cyano complexes), 216 Metal derivatives of organofluorine compounds, 217 IV-Metal derivatives, 218 Metal dusts, 220 Metal fires, 222 Metal fulminates, 222 Metal halides, 222 Metal—halocarbon incidents, 225 Metal halogenates, 226 Metal hydrazides, 226 Metal hydrides, 226 Metal hypochlorites, 228 Metallurgical sample preparation, 228 Metal nitrates, 229 Metal nitrites, 231 Metal nitrophenoxides, 232 Metal non-metallides, 232 Metal oxalates, 233 Metal oxides, 234 Metal oxohalogenates, 236 Metal oxometallates, 236 Metal oxonon-metallates, 237 Metal perchlorates, 238 Metal peroxides, 239 Metal peroxomolybdates, 240 Metal phosphinates, 240 Metal phosphorus trisulfides, 240 Metal picramates, 241 Metal pnictides, 241 Metal polyhalohalogenates, 241 Metal pyruvate nitrophenylhydrazones, 241 Metals, 242 Metal salicylates, 243 Metal salts, 243 Metal sulfates, 244 Metal sulfides, 244 Metal thiocyanates, 246 Metathesis reactions, 246 Microwave oven heating, 246 Mild steel, 247 Milk powder, 248... 

Castro and Kray have reduced the isomeric butenyl chlorides, using chromous sulfate (5). Again, allylic radicals were proposed as intermediates in the reaction. However, unlike the tin hydride reductions, 1-butene was obtained almost exclusively from each of the isomeric chlorides. The process has been described as occurring within a chromium complex. The preponderant formation of 1-butene from butenyl metal complexes has also been noted by others (12, 23, 46). 

---