Sodium Hypochlorite, Bleach, NaOCl
Sodium hypochlorite is an inexpensive, strong oxidizing agent, that is used as disinfectant and bleaching agent. It is unstable as a solid, but solutions of up to 40% are commercially available that contain NaOH and NaCl as byproducts of the preparation:
2 NaOH + Cl2 → NaCl + NaOCl + H2O
Hypochlorite solutions liberate toxic gases such as chlorine when acidified or heated. The reaction with ammonia or with substances that can generate ammonia can produce chloramines which are also toxic and have explosive potential.
Name Reactions
Recent Literature
A general procedure for the osmium-catalyzed dihydroxylation of various
terminal and internal olefins using bleach as cheap oxidant yields the
corresponding cis-1,2-diols in the presence of dihydroquinine or
dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo-
and enantioselectivities under optimized pH conditions.
G. M. Mehltretter, S. Bhor, M. Klawonn, C. Döbler, U. Sundermeier, M. Eckert,
H.-C. Militzer, M. Beller, Synthesis,
2003, 295-301.
Promising, dual-functioning chiral catalysts for the highly enantioselective
epoxidation of α,β-unsaturated ketones gave epoxy chalcones in excelllent
yield and high enantioselectivity using 13% NaOCl as oxidizing agent in
toluene under mild phase-transfer conditions.
T. Ooi, D. Ohara, M. Tamura, K. Maruoka, J. Am. Chem. Soc., 2004,
126, 6844-6845.
Readily available Mn(III) complexes catalyze alkene epoxidation by bleach in
good yields. A highly enantioselective epoxidation catalyst was developed
through a logical sequence of ligand modifications.
E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng, J. Am. Chem.
Soc., 1991,
113, 7063-7064.
