ChemInform Abstract: POLYVALENTE ORGANOJODVERBINDUNGEN 8. MITT. EINFACHE SYNTHESE VON PHENYLJODOSOCARBOXYLATEN

Merkushev, E. B.; Novikov, A. N.; Makarchenko, S. S.; Moskal'chuk, A. S.; Glushkova, V. V.; Kogai, T. I.; Polyakova, L. G.

doi:10.1002/chin.197537174

Cited by 17 publications

(21 citation statements)

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“…31 P NMR and 1 H NMR spectra were recorded with a Varian apparatus at 200 or 500 MHz. Diacetoxyiodobenzene was purchased from Avocado, other diacyloxyiodobenzenes were prepared by a method described in literature [16].…”

Section: Methodsmentioning

confidence: 99%

Reactivity of diacyloxyiodobenzenes toward trivalent phosphorus nucleophiles

Makowiec

Rachoń

2003

Heteroatom Chemistry

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Section: Methodsmentioning

confidence: 99%

Reactivity of diacyloxyiodobenzenes toward trivalent phosphorus nucleophiles

Makowiec

Rachoń

2003

Heteroatom Chemistry

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“…Next, the use of other hypervalent iodine compounds than PIDA was tested as this would deliver other amides than those based on acetic acid and therefore broaden the scope of the methodology (Table 7). These hypervalent iodine compounds were easily prepared by an exchange reaction on PIDA with the respective carboxylic acid 13,22. Subsequently, they were tested in a reaction with 7a as model substrate (Table 7).…”

Section: Resultsmentioning

confidence: 99%

“…By using other hypervalent iodine reagents than PIDA, although not investigated yet, also other amides than secondary acetamides should be accessible. The required bis(acyloxy)(phenyl)‐λ 3 ‐iodanes can be easily obtained by an exchange reaction of the acetate groups in PIDA with carboxylic acids 13. The N ‐substituted amidine substrates are easily accessible from nitriles via the corresponding imidate salts (Pinner reaction) or via a direct approach using activation by Lewis acids 14.…”

Section: Introductionmentioning

confidence: 99%

Cover Picture: Combustion of Boron Particles in Premixed Methane/Air Flames (Prop., Explos., Pyrotech. 2/2016)

Veith

Pfitzner

2016

Propellants Explo Pyrotec

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In this work an efficient tandem process transforming N‐substituted amidines into secondary amides has been described. The process involves N‐acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)‐λ3‐iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyliodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N‐substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.

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“…1,2 As with other bis(acyloxy)iodoarenes, the "T-shaped" structure observed in the solid state is maintained in solution. Moreover, a [1,3] sigmatropic shift of iodine between the two oxygens of the carboxylic acid ligand occurs. 3 Handling, Storage, and Precautions: stable compound that can be stored at room temperature for a long period without decomposition.…”

Section: Bis(22-dimethylpropanoatoκ-o)phenyl-iodinementioning

confidence: 99%