Synthesis ( IF 2.2 ) Pub Date : 2018-09-26 , DOI: 10.1055/s-0037-1610996 Juan Tian 1 , Dayong Sang , Xiaodong Tu , Zhoujun He , Ming Yao
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Abstract
Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
中文翻译：
三碘化铝-二甲基亚砜裂解邻苯二酚单烷基醚
摘要
以丁子香酚和香兰素为模型底物，开发了一种裂解邻羟基苯烷基醚的实用方法。由三碘化铝和二甲基亚砜原位生成的碘化氧化铝（O = AlI）是反应性的醚裂解物质。该方法适用于邻苯二酚单烷基醚以及常规的苯基烷基醚，用于去除甲基，乙基，异丙基和苄基。在最佳条件下，可以很好地耐受各种官能团，例如烯基，烯丙基，酰胺，氰基，甲酰基，酮基，硝基和卤素。在4-溴愈创木酚的去甲基化过程中观察到部分加氢溴化作用，并使用过量的DMSO作为除酸剂解决了该问题。这种方便，有效的程序将是制备邻苯二酚的实用工具。
以丁子香酚和香兰素为模型底物，开发了一种裂解邻羟基苯烷基醚的实用方法。由三碘化铝和二甲基亚砜原位生成的碘化氧化铝（O = AlI）是反应性的醚裂解物质。该方法适用于邻苯二酚单烷基醚以及常规的苯基烷基醚，用于去除甲基，乙基，异丙基和苄基。在最佳条件下，可以很好地耐受各种官能团，例如烯基，烯丙基，酰胺，氰基，甲酰基，酮基，硝基和卤素。在4-溴愈创木酚的去甲基化过程中观察到部分加氢溴化作用，并使用过量的DMSO作为除酸剂解决了该问题。这种方便，有效的程序将是制备邻苯二酚的实用工具。
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