Studies of benzylisoquinolines. Comparison of the reactivity of the methylene group in 1-benzyl and 4-benzylisoquinolines

While examining the oxidation of 4-benzylisoquinolines to the corresponding 4-benzoylisoquinolines as well as the reactivity of these ketones towards hydroxylamine, reduction reagents and Grignard's reagents, there was found a definite difference in the behavior of the methylene group for these compounds as compared to that of papaverine (1-benzylisoquinolines).