Organoiodine heterocycles

The Synthesis of Heterocyclic Compounds with Hypervalent Organoiodine Reagents... 

Applications to the synthesis of heterocyclic compounds of hypervalent organoiodine reagents are covered by Gerald Koser (University of Akron, Ohio) who is well known for his own book in the field. The present review provides continuity with the earlier comprehensive treatment of the subject by Moriarty and Prakmash in Volume 69 of Advances in Heterocyclic Chemistry, which covered the field up through 1996. 

Syntheses of heterocyclic compounds with hypervalent organoiodine reagents 04AHC(86)225. 

Koser, G. F., The Synthesis of Heterocyclic Compounds with Hypervalent Organoiodine Reagents, 86, 225. 

Organoiodine(V) compounds are represented by several common classes shown in Figure 1.3 all these compounds have found application as efficient oxidizing reagents. Particularly important in organic synthesis are noncyclic iodylarenes 18, numerous five-membered heterocyclic benziodoxole derivatives 19 and 20, including IBX and DMP (Table 1.1), pseudocyclic iodylarenes 21-23 and cyclic or pseudocyclic derivatives of 2-iodylbenzenesulfonic acid, 24-26. 

Organoiodine(V) heterocycles are represented by several typical classes 78—86 shown in Figure 15. The most important representative of these compounds, 2-iodoxybenzoic acid (IBX, 78), was originally reported in 1893 (1893CB1727). The cycHc structure of IBX derivatives was confirmed by an X-ray crystallographic study in the work of A. R. Katritzky and coworkers (1990JCS(P2)1657). 

---