ChemInform Abstract: OZONOLYTIC FRAGMENTATION OF PHENYLIODONIUM β‐DIKETONATES; A CONVENIENT SYNTHESIS OF UNSOLVATED VIC‐TRIKETONES

Abstract

Cyclische und acyclische β‐Diketone (I) werden mit IodosobenzoI‐diacetat (II) in Phenyliodoniumylide (III) übergeführt, die mit Ozon zu vic‐Triketonen (IV) oxidiert werden.

Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents

“…As shown in Scheme 4 the iodonium ylide 4 of dibenzoylmethane [ 12 , 13 ] was prepared quantitatively by the reaction of 1 with (diacetoxyiodo)benzene in the presence of KOH in MeCN, according to the recently reported literature method [ 14 ]. The iodonium ylide 4 was used directly to the next reaction without further purification due to the instability towards purification processes.…”

Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides

“…The phenyliodonium ylide 5b was synthesized by reaction of the hydrocarbon 5a [ 10 ] with PhI(OAc) 2 [ 11 ]. Exposure of 5b to [Cu(OTf) 2 ] in CH 2 Cl 2 at 0° C in the presence of chiral ligands A – E resulted in intramolecular CH insertion and afforded the cyclopentanone carboxylate 6 .…”

Hypervalent Iodine Compounds as Potent Antibacterial Agents against Ice Nucleation Active (INA)Pseudomonassyringae

“…The inner salt 1o was prepared from o-iodobenzoic acid according to an established method (27). Ylides 2a-c are stable iodonium ylides and were prepared from the corresponding dicarbonyl compounds and the proper (diacetoxyiodo)arene (28). Addition of trifluoroacetic acid to ylides 2a and 2b afforded the corresponding iodonium salts 1m and 1n.…”