Na. Noureldin et al., HETEROGENEOUS PERMANGANATE OXIDATIONS .7. THE OXIDATION OF ALIPHATIC SIDE-CHAINS, Journal of organic chemistry, 62(25), 1997, pp. 8767-8772
Alkylbenzene side chains are oxidized at the benzylic position when tr
eated under heterogeneous conditions with permanganate adsorbed on a s
olid support. The products are alcohols if the benzylic carbon is tert
iary, or ketones if it is secondary. Carbon-carbon bond cleavage, whic
h usually occurs when these same compounds are oxidized by permanganat
e under homogeneous conditions, does not occur. A unique selectivity i
s observed for the oxidation of derivatives of indane, 1, and tetralin
, 2, in which one of the methylenes is replaced by an oxygen. If the o
xygen is in the alpha-position, no reaction occurs; if it is in the be
ta-position; good yields of the corresponding lactone are obtained. A
mechanism consistent with the observed selectivity has been proposed.