Abstract
This chapter examines various reactions of interest in medicinal chemistry. The properties of 1-chlorobenzotriazole, capable of effecting high-yield oxidations of alcohols to aldehydes and ketones, as well as other reactions, have been described. Oxidation occurs on refluxing in CCl 4 for a short time and is believed to occur via a radical chain mechanism. A large number of 1,4-, 1,5-, and 1,6-diols is converted to lactones on treatment with silver carbonate on celite in refluxing benzene mevalonolactone is thus prepared in 74% yield. An ingenious method for the oxidation of primary amines modeled after biological transamination reactions has been developed. Et 3 SiH in the presence of Pd is usable in a convenient way to effect the conversion of acyl chlorides to aldehydes in higher yields than are obtainable with lithium hydrides. The isolation of [Py 2 .DMF.RhCl 2 (BF 4 )], a highly active chloroform-soluble catalyst that gives the same product stereochemistry observed in heterogenous hydrogenation, has also been described.
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