402-23-3Relevant articles and documents
[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
supporting information, p. 890 - 895 (2021/02/01)
A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.
Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions
Jereb, Marjan,Zupan, Marko,Stavber, Stojan
scheme or table, p. 555 - 566 (2009/09/06)
The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.
Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders
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Page/Page column 97, (2010/02/14)
Aryl sulfonamide and sulfonyl compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.