212373-96-1Relevant articles and documents
Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate
Kataoka, Tadashi,Watanabe, Shin-Ichi,Yamamoto, Keiichirou,Yoshimatsu, Mitsuhiro,Tanabe, Genzoh,Muraoka, Osamu
, p. 6382 - 6386 (2007/10/03)
The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)l selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and 77Se high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.