Organic Syntheses, Coll. Vol. 5, p.658 (1973); Vol. 43, p.60 (1963).
Caution! This compound explodes if heated to 210°.
Finely ground iodosobenzene diacetate2 (32.2 g., 0.10 mole)
is placed in a 250-ml. beaker
, and 150 ml. of 3N sodium hydroxide
is added over a 5-minute period with vigorous stirring. The lumps of solid that form are triturated with a stirring rod
for 15 minutes, and the reaction mixture stands for an additional 45 minutes to complete the reaction. One hundred milliliters of water is added, the mixture is stirred vigorously, and the crude, solid iodosobenzene
is collected on a Büchner funnel
. The wet solid is returned to the beaker and triturated in 200 ml. of water. The solid is again collected on the Büchner funnel, washed there with 200 ml. of water, and dried by maintaining suction. Final purification is effected by triturating the dried solid in 75 ml. of chloroform
in a beaker. The iodosobenzene
is separated by filtration (Note 1)
and air-dried; weight 18.7–20.5 g.
); m.p. 210°
shows the product to be more than 99% pure (Note 2)
The filtrate yields unreacted diacetate on evaporation.
The purity of the iodosobenzene
depends on the purity of the diacetate used.
4. Merits of the Preparation
The procedure seems to be a general way of preparing iodosoarenes with electron-donating substituents, for the submitters have used it to obtain good yields of o-, m- and p-iodosotoluene
, 2- and 4-iodoso-m-xylene
, and 4-iodosobiphenyl
Iodosoarenes are useful in the preparation of iodonium salts, Ar2
This preparation is referenced from:
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