Indanones and indenols from 2-alkylcinnamaldehydes via the intramolecular Friedel-Crafts reaction of geminal diacetates.
Indanones and indenols from 2-alkylcinnamaldehydes via the intramolecular Friedel-Crafts reaction of geminal diacetates.
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DOI：
10.1021/jo900910b
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发表时间：
2009-07
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通讯作者：
Gary B. Womack;John G. Angeles;Vincent E. Fanelli;Brinda Indradas;R. Snowden;P. Sonnay
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文献类型：
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作者：
Gary B. Womack;John G. Angeles;Vincent E. Fanelli;Brinda Indradas;R. Snowden;P. Sonnay
当在4- 6mol%FeCl_3存在下，于室温下用Ac_2O处理时，2-烷基肉桂醛通过偕二乙酸酯中间体转化为2-烷基-1H-茚-1-基乙酸酯。乙酸茚酯的甲醇分解产生相应的茚醇。皂化产生2-烷基茚酮，实际上提供了使用催化水平的酸的分子内酰化。
When treated with Ac2O at rt in the presence of 4-6 mol % FeCl3, 2-alkylcinnamaldehydes are converted to 2-alkyl-1H-inden-1-yl acetates through the intermediacy of gem-diacetates. Methanolysis of the indenyl acetates yields the corresponding indenols. Saponification yields 2-alkylindanones, providing, in effect, an intramolecular acylation employing catalytic levels of acid.