Synthesis and Acid-Catalyzed Transformations of Mercurial Solvent Adducts of 2-Nitrobenzylcyclopropane. First Stable Metalated 1-Oxo-3,4-dihydro-1H-2,1-benzoxazinium Ionsстатья
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Дата последнего поиска статьи во внешних источниках: 6 февраля 2014 г.
Аннотация:Adduct of solvomercuration of 2-nitrobenzyl-, 2-nitro-4,5-(ethylenedioxy)ben¬zyl-, and 4,5-dimethoxy-2-nitrobenzylcyclopropanes were synthesized. The inforaction of these adducts with sulfuric, fluorosulfonic, or chlorosulfonic acid gives 3-(2-chloromercurio)ethyl-I-oxo-3,4-dihydro-IH-2,I-benzoxazinium ions whose stability depends on the nature ofsubstituents in the aromatic ring. Unstable metalated l-oxo-3,4-dihydro-IH-2,I-benzoxazinium ions underwent fast protodemercuration to form metal-free 3-ethyl-I-oxo-3,4-dihydro-IH-2,I-benzoxazinium ions. Stable analogs in the above acids are not changed appreciably over a period of 48-72 h. Hydrolysis of stable metalated l-oxo-I,3-dihydro-2,I-benzoxazolium ions results in 4-chloro¬mercurio-I-(2-nitroaryl)butan-2-ol only.