Tetraethylammonium periodate

C-Nitrosocarbonyl compounds RCONO (R = Me or Ph), generated from hydroxamic acids and tetraethylammonium periodate, readily react with dienes such as butadiene and... 

One of the earliest examples of its application describes the oxidation with tetraethylammonium periodate of oximes to nitroso compounds [21, 22] and the same reagent has subsequently be used in the preparation of the transient nitroso compounds by oxidation of A-hydroxyureas [21, 22] and benzhydroxamic acids [26],... 

Tetraethylammonium periodate, ( 2115)419104 . Mol. wt. 321.16, m.p. 176-177° soluble in H2O and in many common organic solvents, namely CH3COOH, acetone, pyridine, CHCI3, DMF insoluble in ether and benzene. The material was first prepared by Qureski and Sklarz, who observed that the reagent was equivalent to NaI04 for oxidation of N-alkylhydroxylamines to nitroso compounds. They suggested that the solubility in both water and many organic solvents could be useful for certain oxidations. 

Kirby et al. have used tetraethylammonium periodate for oxidation of hy-... 

Similarly, V-alkoxycarbonylhydroxvlamincs can also be converted into the corresponding nitroso derivatives which are trapped by 1,3-dienes to form the corresponding alkyl 3,6-dihy-dro-2fl-l,2-oxazine-3-carbOxylates 1. The reaction is generally performed by addition of the A -alkoxycarbonylhydroxylarnine to tetraethylammonium periodate at 0 C in the presence of the appropriate diene29. 

To a stirred solution of 0.99 mmol of the cyclopentadienc and 0.66 mmol of the appropriate V-acylhydroxyl-amine in 8 mL of distilled CH,OH at — 50 °C is added slowly (over ca. 1 h) a solution of 0.73 mmol of tetraethylammonium periodate in 5 mL of distilled CH3OH. The cold reaction mixture is then poured into Ta,S205 solution. Extraction with F.tOAc, followed by drying and evaporation, gives the crude product which is purified by flash column chromatography. 

The nitroso urea 1, derived from D-bornane-10,2-sultam. has been shown to be useful in asymmetric hetero-Diels Alder cycloaddilions. It can be generated in situ by oxidizing the corresponding jV-hydroxyurea with tetraethylammonium periodate in dichloromethane at 20 °C. In the presence of a five-fold excess of 1,3-cycloalkadiene, the corresponding adducts 2 are obtained in good yield and complete facial stereoselectivity104. 

Scheme 2 (i) Tetranitromethane, methanolic ammonia, rt (ii) Zn, NH4C1, MeOH, reflux (iii) 2 N HC1 (iv) 1-chloro-l-nitrosocyclohexane (v) aqueous methanolic HC1, yield over steps iv, v, ii 35% (vi) benzohydroxamic acid, tetraethylammonium periodate, 97%... 

Tetraethenyl-2,4,6,8-tetramethylcyclotetrasiloxane. 3560 Tetraethylammonium perchlorate, 3088 Tetraethylammonium periodate, 3090 Tetraethyldiarsane, 3087... 

The preparation of tetraethylammonium periodate and its chloroform solubility have been reported. Little other work has been done, however, with periodate anion as an oxidant in aprotic organic solvents [16]. 

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