โ Scribed by Vakaba Toure; Michele Levy; Petr Zuman
No coin nor oath required. For personal study only.
In cyclic systems, where the electroactive group is directly attached to the ring, the electrolytic properties can be affected either by a substituent in the ring system, or by the ring size and the stereochemistry of the system.
Monocyclic systems, investigated so far, such as cycloalkanones 1, their betainylhydrazones 2, 2-(piperidinomethyl) cycloalkanones 3 and cycloalkylbromides 4, 5 are reduced at such negative potentials that use of buffered systems is in general prevented and hence the amount of available information on mechanism is limited.
Our experience with aryl alkyl ketones 6-1ยฐ and with reduction of phthalimide 11 indicated that benzocyclenones I-III would be useful models. The literature reported only reducibility and half-wave potentials of indanone ~ 2 (I) and tetralone 13 (II), but their reduction process has not been compared. CO (I) n:l I'~ ~CH2 (rr) n: 2 ~I'~-/:'L'"-(CH2)( (Ill') n = 3
Preliminary experiments have shown (Fig. ) that polarographic curves at pH 3 and 6.4 of the three compounds studied show little resemblance. It was thus necessary to study all three compounds in detail to prove whether their different behavior is due to quantitative differences in a single mechanism or to qualitatively different mechanisms operating in each individual case.
EXPERIMENTAL
Polarographic current-voltage curves were recorded by means of a Cambridge
๐ SIMILAR VOLUMES
## Misinterpretations regarding the selectivity of tetraalkylammonium borohydride reductions in dichloromethane are resolved. Tetrabutylamnonium borohydride offers several advantages, but both it and tetraethylammonium borohydride are highly useful synthetic reagents.