Iodosobenzene diacetate: Benzene,

Peracetic acid, far oxidation of iodo-benzene to iodosobenzene diacetate, 43, 62... 

Alcohols with a hydrogen in the 8 position can be cychzed with lead tetraace-tate. ° The reaction is usually carried out at 80°C (most often in refluxing benzene), but can also be done at room temperature if the reaction mixture is irradiated with uv light. Tetrahydrofurans are formed in high yields. Little or no four- and six-membered cyclic ethers (oxetanes and tetrahydropyrans, respectively) are obtained even when y and s hydrogens are present. The reaction has also been carried out with a mixture of halogen (Br2 or I2) and a salt or oxide of silver or mercury (espe-cially HgO or AgOAc), with iodosobenzene diacetate and I2, and with ceric... 

DinitTO-3,3 -dichloTOazobenz ne, om prisms (from benz), mp 266.5-67.2° obtd by oxidizing 2-nitro-3-chloroaniline in dry benzene with iodosobenzene diacetate (Ref 5)... 

Oxidative cyclization. The reaction of 2,2 -diaminodiphenylmethanes (1) with iodosobenzene diacetate in benzene at room temperature for several days affords dibenzo-[c,f]-[l,2]diazepines (2) in 30-60% yield.2 The reaction is not applicable to 2,2 -diaminobenzophenones. 

Photolysis of alkyl carboxylic acids with lead (IV) acetates can generate alkyl radicals by decarboxylation and this has been used to place an aryl group on a cubane. Thus photolysis of a benzene solution of the cubane dicarboxylic acid (136) containing lead tetraacetate yields the phenyl cubane (137). A mechanistically related procedure uses iodosobenzene diacetate for the photochemical arylation of cyclohexane carboxylic acid with heteroaromatics such as pyridine or quinoline. 

The classical permanganate oxidation of a-pinene yields cis-pinonic acid (383). Now, using dicyclohexyl-18-crown-6 ether in benzene, the yield has been raised to 90%. In the conventional oxidation, the yield of the acid (383) is very low, but in the neutral part the interesting ether (384) has been found. This is quantitatively dehydrated by thionyl chloride to (385), which has led to the synthesis of ( - )-7-epichrysanlhenol (386), the structure of which was linked to chrysanthe-none by oxidation. It has been noted that with iodosobenzene diacetate and... 

A mixture of di-(2-amino-4-chlorophenyl) sulfone, iodosobenzene diacetate, and dry benzene stored 3 days at room temp. cyclic azo compound. Y 71%. H. H. Szmant and R. Infante, J. Org. Ghem. 26, 4173 (1961). 

Iodosobenzene explodes violently at about 220 °C, so that determinations of the melting point should not be attempted. It may, however, be converted into iodobenzene diacetate in the following manner. Dissolve 2g of iodosobenzene in 6 ml of glacial acetic acid boiling is usually necessary. Cool. The resulting diacetate is readily soluble in acetic acid but is insoluble in ether. Add about 50 ml of ether in order to precipitate the iodobenzene diacetate. Filter and wash with ether. The yield is 2g, m.p. 157°C. It may be recrystallised from benzene, and will keep indefinitely (unlike the iodobenzene dichloride). 

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