PREPARATION OF ALPHA- OR BETA-SUBSTITUTED -DELTAALPHA,BETA-OR DELTABETA-,GAMMA-BUTENOLIDE

摘要

PURPOSE:To obtain the titled compound for a germicide and insecticide, by oxidizing a novel alpha- or beta- substituted -gamma-phenylthio-gamma-butyrolactone as a starting material with m-chloroperbenzoic acid, and removing the phenylsulfinyl group from the resultant compound with pyridine. CONSTITUTION:An alpha- or beta-substituted -gamma-phenylthio-gamma-butyrolactone of formula I (R1 and R2 are H, alkyl, phenyl, benzyl, or either one of R1 and R2 is H) is oxidized with m-chloroperbenzoic acid to give the corresponding gamma-phenylsulfinyl compound, and the phenylsulfinyl group of the resultant compound is then removed with pyridine to give the aimed compound of formula II. The novel compound of formula I is obtained by hydrolyzing and decarboxylating a compound of formula III, oxidizing the resultant compound of formula IV with an oxidizing agent, and subjecting the novel oxidized compound of formula V to the Pummerer rearrangement in the presence of acetic anhydride and an acid catalyst.