Aryliodonium ylides

TransyUdation. Aryliodonium ylides of the ArI=CHTf2 type can be prepared from heating Arl (in large excess) with PhI=CHTf2 and Rh2(OAc)4 at 90°. ... 

Alkylidenephosphoranes containing the bis(aiy]/all9lsulfonyl)niethylene functionality may be obtained from aryliodonium ylides and triphenylphosphine, a caitene mechanism Hesumably being involved. ... 

Experimental procedure for the thermolysis of aryliodonium ylides. Preparation of 40 (Scheme 18.31) A suspension of 133 (1 mmol) and benzyl amine (1 mmol) in CH2CI2 (15 mL) was refluxed for 4-7 hours until a clear solution resulted and TLC showed the disappearance of the starting ylide. The solution was concentrated in a vacuum to half its volume, hexanes (10 mL) were added, and the precipitated yellow solid was filtered and washed repeatedly with hexanes. The amide 140 (mp 144-146°C) was obtained in 84% yield. An analytical sample was obtained by recrystalUzation from CH2Cl2-hexanes. 

The rearrangement of aryliodonium ylides was used by Mehta and Singh to prepare the required starting material... 

Malamidou-Xenikaki E, Spyroudis S, Tsanakopoulou M. Studies on the reactivity of aryliodonium ylides of 2-hydroxy-l,4-naphthoquinone reactions with amines. J. Org. Chem. 2003 68 5627-5631. 

Preparation Aryliodonium imides 463 are usually prepared by the reaction of (diace-toxyiodo)arenes with the respective amides under basic conditions (Scheme 2.133) [623]. Most iodonium imides are relatively unstable at room temperature and their storage under an inert atmosphere at low temperature is recommended. Exothermic decomposition frequently occurs at the melting point of ylides and some of them were even claimed to be explosive [623]. 

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