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- W2093671454 abstract "Reactions of 2-methoxy-3-methyl-1,4-benzoquinone with various (E)-1-propenylbenzenes promoted by 1 equiv of Ti(IV), as a 1:1 mixture of TiCl4−Ti(O-i-Pr)4, produce rel-(1S,6R,7R,8R)-8-aryl-4,7-dimethyl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5-diones 3 and trans-2-aryl-3,7-dimethyl-6-methoxy-2,3-dihydro-5-benzofuranols 5 as the major products. Reactions promoted by 2 equiv of Ti(IV) as a 1:1 mixture of TiCl4−Ti(O-i-Pr)4 or 1 equiv of either TiCl4, SnCl4, or BF3·OEt2 give regioisomeric rel-(1R,6S,7R,8R)-7-aryl-4,8-dimethyl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5-diones (4) and/or trans-2-aryl-3,6-dimethyl-7-methoxy-2,3-dihydro-5-benzofuranols (6). A mechanism involving regioselective coordination of the various Lewis acids to the quinone is used to explain the formation of the products. These reactions demonstrate the effective regiocontrol exerted over the reactions by the nature of the Lewis acid promoters. Cyclobutanes 3 and 4 cleanly undergo rearrangement to the corresponding benzofuranols 5 and 6 on treatment ..." @default.
- W2093671454 created "2016-06-24" @default.
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- W2093671454 date "2010-06-20" @default.
- W2093671454 modified "2023-09-25" @default.
- W2093671454 title "ChemInform Abstract: Lewis Acid Directed Reactions of Quinones with Styrenyl Systems: The Case of 2-Methoxy-3-methyl-1,4-benzoquinone." @default.
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- W2093671454 doi "https://doi.org/10.1002/chin.199832050" @default.
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