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Aluminum Triiodide‐Mediated Cleavage of o ‐Hydroxyphenyl Alkyl Ethers Using Inorganic Bases and Metal Oxides as Acid Scavengers
Author(s) -
Tian Juan,
Yi Cuicui,
He Zhoujun,
Yao Ming,
Sang Dayong
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701685
Subject(s) - triiodide , chemistry , guaiacol , catechol , scavenger , alkyl , eugenol , metal , organic chemistry , inorganic chemistry , nuclear chemistry , radical , catalysis , electrode , dye sensitized solar cell , electrolyte
Abstract Studies have shown that a proper acid scavenger is a requisite to prevent acid‐labile functional groups from deterioration during aluminum triiodide‐mediated cleavage of o ‐hydroxyphenyl alkyl ethers. In this work, the acid scavenging effect of inexpensive and bench stable inorganic bases and metal oxides were evaluated using eugenol as a model substrate. Among the bases and oxides screened, KO t Bu, Na 2 CO 3 , CaO, CuO and ZnO were found effective. The method is compatible with a variety of functional groups, and was applied successfully in cleaving catechol monoethers such as guaiacol, vanillin, isovanillin, vanillonitrile, isovanillonitrile, acetovanillone, nonivamide, ethylvanillin and o‐ isopropoxyphenol. The corresponding catechols were obtained in excellent yields. The oxophilicity of aluminum triiodide is not markedly suppressed by these inorganic acid scavengers, making the aluminum triiodide‐acid scavenger method effective in cleaving general phenyl methyl ethers such as m ‐guaiacol, 4‐allylanisole, veratraldehyde and methyl eugenol without the anchimeric assistance of an o‐hydroxyl group.