Benziodoxole-based hypervalent iodine

Benziodoxole-based hypervalent iodine reagents in organic synthesis 05COS121. 

Hydroxybenziodoxole 104 can be readily converted into its acetoxy derivative, l-acetoxy-1,2-benziodoxole-3(l//)-one (88, 2X = O, Y = OAc), by heating 104 with acetic anhydride and the acetoxy derivative can be further converted into the alkoxy derivatives by treatment with an appropriate alcohol [280], The tetrabutylanmionium salt of hydroxybenziodoxole 104 has been prepared by the reaction of hydroxybenziodoxole with tetrabutylammonium fluoride in THF it is a mild oxidant that is useful for the preparation of epoxides from a,p-unsaturated carbonyl compounds [281], l-Hydroxy-l,2-benziodoxole-3(l//)-one and l-acetoxy-l,2-benziodoxole-3(l//)-one have found wide application as starting compounds for the synthesis of various benziodoxole-based hypervalent iodine reagents by ligand exchange on iodine [239]. 

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