A new synthesis of o-quinonemethides and their inter- and intramolecular cyclization reactions.
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概要
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The reaction of <I>o</I>-[1-(alkylthio)alkyl]phenols with silver(I) oxide at room temperature generated <I>o</I>-quinonemethides in good yields along with silver alkanethiolate. This mechanism, based upon one-electron oxidation, is excluded in view of several experimental facts. The resulting <I>o</I>-quinonemethides reacted efficiently with ethyl vinyl ether to afford <I>cis</I>-chromans as the result of endo cycloaddition between (E)-<I>o</I>-quinonemethides and the ether. Similarly, <I>o</I>-[1-(alkylthio)allyl]phenols were converted to <I>cis</I>-chromans via the corresponding (<I>E</I>)-<I>o</I>-quinonemethides (6-allylidenecyclohexadienone). In the absence of dienophiles, some chromenes were obtained from the allylphenols.
- 公益社団法人 日本化学会の論文
著者
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Inoue Tsutomu
Department Of Nephrology Saitama Medical School
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Sato Kikumasa
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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Inoue Seiichi
Department Of Applied Chemistry Faculty Of Engineering Yokohama National University
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