- A new efficient method for the conversion of aldehydes into nitriles using ammonia and hydrogen peroxide
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Aldehydes were converted into the corresponding nitriles by a homogeneous reaction with ammonia and aqueous hydrogen peroxide in the presence of copper salts or complexes under mild conditions. (C) 2000 Elsevier Science Ltd.
- Erman,Snow,Williams
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p. 6749 - 6752
(2007/10/03)
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- The Introduction of Nitrile-Groups into Heterocycles and Concversion of Carboxylic Groups into their Corresponding Nitriles with Clorosulfonylisocyanate and Triethylamine
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Addition of chlorosulfonylisocyanate (CSI) to heterocycles such as thiophene (4) or indole (15) and unsaturated systems such as dihydropyran (7) gives N-chlorosulfonylamides RCONHSO2Cl, which can be converted by equivalent amounts of triethylamine to their corresponding nitriles.Since carboxylic acids react with CSI to N-chlorosulfonylamides, subsequent treatment with triethylamine affords the corresponding nitriles, but no isocyanates as claimed by other authors.The mechanisms of the conversion of the intermediate N-chlorosulfonylamides into the corresponding nitriles are discussed.
- Vorbrueggen, Helmut,Krolikiewicz, Konrad
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p. 6549 - 6558
(2007/10/02)
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- Improved Synthesis of 3-Methylcholanthrene
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An improved synthesis of 7-methylindan-4-yl 1-naphthyl ketone (3), an important precursor of 3-methylcholanthrene (1), has been developed.The key intermediates for 3, 4-cyano-7-methylindan (2a) and 4-(ethoxycarbonyl)-7-methylindan (2b), were conveniently prepared in high yields by reaction of 1-(1-pyrrolidino)cyclopentene (6) with sorbonitrile (5a) or ethyl sorbate (5b), followed by aromatization with sulfur. 1-Naphthylmagnesium bromide (4b) in the presence of cuprous iodide reacted cleanly with 4-(chloromethanoyl)-7-methylindan (12) to give 3.The Friedel-Crafts acylation of naphthalene with 12 afforded 84percent of 3 and 16percent of β isomer 13.Alternatively, 3 was prepared in 75percent yield by condensation of Grignard reagent 4b with 2a in THF.Thermal annelation of 3 afforded 1 in 41.5percent yield.
- Tang, Ping Wah,Maggiulli, Cataldo A.
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p. 3429 - 3432
(2007/10/02)
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