1,3-DIPHENYLPROPANE-1,3-DIAMINES XII - A NOVEL-APPROACH TO STEREODEFINED OXIMES AND OXIME ETHERS OF MONOTHIOKETALIZED 1,3-DIKETONES AND THEIR CONVERSION TO 3-AMINOOXIMES

Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochlori de affording mixtures of (E/Z) isomers which are hard to separate or a n even unseparable. Isomerically pure oximes and O-methyloximes, howev er, are obtained either from 2-lithiated 1,3-dithianes and alpha-halog eno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated o xime ethers and dithienium salts. Reduction, acetylation, hydrolysis o f the ketal increment, and oximation afford 3-amino-oximes which are p recursors of 1,3-diphenylpropane-1,3-diamines.