1028800-86-3Relevant academic research and scientific papers
New highly soluble dimedone-derived iodonium ylides: Preparation, X-ray structure, and reaction with carbodiimide leading to oxazole derivatives
Zhu, Chenjie,Yoshimura, Akira,Solntsev, Pavlo,Ji, Lei,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 10108 - 10110 (2012/11/13)
Highly soluble dimedone-derived o-alkoxyphenyliodonium ylides have been prepared and characterized by single crystal X-ray diffraction. These new iodonium ylides are useful reagents for the preparation of oxazole derivatives by reaction with carbodiimides. The Royal Society of Chemistry 2012.
The mechanism of 1,4 alkyl group migration in hypervalent halonium ylides: The stereochemical course
Moriarty, Robert M.,Tyagi, Sachin,Ivanov, Daniela,Constantinescu, Mircea
, p. 7564 - 7565 (2008/12/22)
Rhodium(II)-acetate-catalyzed decomposition of either 1,3-cyclohexanedione phenyliodonium ylide or 5,5-dimethyl-1,3-cyclohexanedione phenyliodonium ylide in the presence of alkyl halides yields the corresponding 3-alkoxy-2-halocyclohex-2-enones via a 1,4 alkyl group migration shown to be concerted and intramolecular. In the case of (S)-α-phenethyl chloride, the rearrangement proceeds with essentially 88.6% retention of configuration. Theoretical calculations at the B3LYP/6-31G level reveal an activation energy of 5.4 kcal/mol for the process. A Claisen-like rearrangement occurs in the case where allylic halides, such as dimethylallyl or methallyl chorides, are used. The mechanistic pathway proposed for these processes involves addition of the halogen atom of the alkyl or allyl halide to the rhodium carbenoid from the iodonium ylide to yield a halonium intermediate that undergoes halogen to oxygen group migration. Aryl halides, such as chloro-, bromo-, iodo-, and fluorobenzene, behave differently under the same reaction conditions, yielding the product of electrophilic aromatic substitution, namely, the 2-(4-halophenyl) 1,3-cyclohexanedione. Copyright
