The title cyclic hypervalent iodine compounds (4-8) were prepared in good yields by the ligand exchange reaction of the acetoxy cyclic iodinanes (1-3) with mmethylsilyl compounds and of the chloro cyclic iodinane (9) with silver nitrate, and were found to be air-stable at room temperam.Recently, hypervalent iodine(1II) compounds have been extensively used in organic syntheses due to their low toxicity, ready availability, and easy handling.'Most of the reported isolable reagents have electron negative halogen or oxygen ligands such as chlom, fluom, acyloxy, hydroxyl, and sulfonyloxy ligands and were useful for the inaoduction of their ligands to a variety of substrates through an oxidation step.Therefore, preparation of iodinanes having novel ligands will enlarge the utilities of hypemalent iodine compounds in synthetic organic chemisny.Although the reagents having one or two azido ligands have been prepared from phenyliodine diacetate or iodosobenzene and TMS-N3, and used for the azidation of various compounds, they are too labile to be isolated and even to be identified by spectroscopic meam2 Reagents having cyano ligands were prepared, however, they are not very stable and must be handled under a nitrogen atmosphere.3We wish to present here the preparation of the cyclic iodinanes (4-8) having azido, cyano, and nitrato ligands, which are crystalline compounds and air-stable at room ternperatwe.4.
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Kita et al. (1996) studied this question.