Morris R. Ort

Methylene bis(aluminum dihalides)

Abstract Methylene bis(aluminum dichloride) and methylene bis(aluminum dibromide) have been synthesized in essentially quantitative yields. It is postulated that the reaction sequence which leads to these compounds requires aluminum monohalide as a transitory intermediate.

Electrolytic Reductive Coupling XVII . A Study of 1,2‐Diactivated Olefins. Part II . Macro‐electrolyses

The electrolytic reductive coupling of a variety of diactivated olefins, , has been studied. The reduced dimeric products have been isolated and carefully identified. Both symmetrical and unsymmetrical dimers were observed. The dimeric products are formed by two paths: the first involves the attack of the electrochemically generated anion radical on unreduced olefin; the second involves the protonation of the anion radical followed by reduction to an anion and subsequent attack on the olefin. The isomer distribution in the dimeric product obtained by the first route is rationalized on the basis of the relative anion stabilizing ability of the activating groups in the acceptor molecule and the relative ability toward stabilizing a radical site in the donor molecule. The possibility of forming cross‐coupled products (between a diactivated olefin and a Michael acceptor) is limited to systems in which the electrochemically generated anion radical is relatively stable toward its parent olefin or in which the reduction potentials of the pair are similar, i.e., .

Electrolytic reductive coupling as a synthetic tool

Abstract The utility of electrolytic reductive coupling as a means for synthesizing a variety of polyfunctional compounds is discussed. Activated olefins function as acceptors towards donors generated by electrolytic induction of (a) other activated olefins, (b) other activated olefinic groups within the same molecule, (c) compounds containing “leaving groups” and (d) azo-compounds and Schiff bases.