The novel oxidant of sodium hypochlorite
pentahydrate (NaOCl·5H2O) crystals is now available
for industrial and laboratory
use. It is superior to conventional aqueous sodium hypochlorite solutions
(aq. NaOCl). The crystalline material is 44% NaOCl and contains minimal
amounts of sodium hydroxide and sodium chloride, and the aqueous solution,
which is prepared from NaOCl·5H2O and water, has a
pH of 11–12. Examples of the selective organic synthesis using
NaOCl·5H2O involve the oxidations of primary and secondary
alcohols, selective oxidations to sulfoxide and sulfone, oxidative
cleavage of disulfide to sulfonyl chloride and bromide, oxaziridine
synthesis, and oxidative dearomatization of phenols.
A practical
method for the preparation of (diacetoxyiodo)arene
ArI(OAc)2 is described. The use of commercially available
sodium hypochlorite pentahydrate (NaClO·5H2O) enabled
safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing
and -donating substituents. The method allows tandem divergent access
to synthetically useful organo-λ3-iodanes such as
hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.
Magnetic field effects (MFEs) on the photoinduced hydrogen abstraction reaction of benzophenone with phenol were investigated in ionic liquids (ILs) with a short alkyl chain (N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)amide (TMPA TFSA)) and long alkyl chains ((N,N,N-trimethyl-N-octylammonium bis(trifluoromethanesulfonyl)amide (TMOA TFSA) and N-decyl-N,N,N-trimethylammonium bis(trifluoromethanesulfonyl)amide (DTMA TFSA)) by a nanosecond laser flash photolysis technique. In each ionic liquid, escaped radical yield of a benzophenone ketyl radical rapidly increased with increasing magnetic field strength (B) of 0 T < B≤ 0.01 T. At 0.01 T < B≤ 0.4 T, the escaped radical yield almost saturated in TMPA TFSA or gradually increased in TMOA TFSA and DTMA TFSA. At much higher fields of 0.4 T < B≤ 30 T, the yield gradually decreased, resulting in 10-15% decrease at 30 T. The observed MFEs can be explained by the hyperfine coupling and Δg mechanisms together with the relaxation mechanism. On the time profiles of the transient absorption observed for the benzophenone ketyl radical, MFEs were generated in the time range of 0 < t < 0.6 μs. The cage lifetimes of TMOA TFSA and DTMA TFSA were estimated to be at least 120 ns.
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