26910-41-8Relevant academic research and scientific papers
Synthesis and allergenic potential of a 15-hydroperoxyabietic acid-like model: Trapping of radical intermediates
Mutterer,Gimenez Arnau,Karlberg,Lepoittevin
, p. 1028 - 1036 (2007/10/03)
To better understand the skin sensitization mechanism of 15-hydroperoxyabietic acid-like compounds, 2-(1'-hydroperoxy-1'-methylethyl)-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene 7 was synthesized. The allergenic activity of this compound was tested on mice using the local lymph node assay, and further evaluated on guinea pigs using the Freund's complete adjuvant test. Using these methods, hydroperoxide 7 was found to be a strong sensitizer. Radical-trapping experiments were carried out on this compound in the presence of the spin-trapping agent, 1,1,3,3-tetramethylisoindolin-2-yloxyl 17, using light to induce radicals. The formation of carbon-centered radicals derived from compound 7 by intramolecular cyclization of an oxygen-centered radical was observed. The reaction of these intermediates with 17 gave various adducts in a very low yield, but a 1/1 mixture of diastereomers 18a and 18b (0.1% yield) was isolated and characterized, together with compound 19 (0.03% yield). The results suggest that carbon-centered reactive radicals are formed from allylic hydroperoxides and that this could be the possible mechanism involved in allergic contact dermatitis to abietic acid.
Solid-Phase Silica-Gel Catalyzed α-Halogenation of Alkyl Aryl Sulfoxides with N-Halosuccinimides
Drabowicz, Jozef
, p. 831 - 833 (2007/10/02)
Alkyl aryl sulfoxides are readily halogenated by silica-gel supported N-halosuccinimides.The conversion of optically active alkyl 4-methylphenyl sulfoxides into 1-haloalkyl 4-methylphenyl sulfoxides is accompanied by inversion of configuration at the S-atom.The stereoselectivity of the solid-phase halogenation of alkyl aryl sulfoxides is much higher than that observrd for the halogenation in solution.
