3-Methylcalix[4]arene: A New Versatile Precursor to Inherently Chiral Calix[4]arenes.

Title3-Methylcalix[4]arene: A New Versatile Precursor to Inherently Chiral Calix[4]arenes.
Publication TypeJournal Article
Year of Publication1996
AuthorsFu, D-K, Xu, B, Swager, TM
JournalJournal of Organic Chemistry
Keywordsmethylcalixarene prepn chiral calixarene, methylcalixarenetetrol prepn chiral calixarene

This paper describes the first synthesis of 3-methylcalix[4]arene, an inherently chiral mol. which can be readily functionalized. The procedure involves hydromethylation of the readily available 4-bromo-3-methylphenol followed by dehydrative cyclization with TiCl4 to give 4-bromo-3-methylcalix[4]arene. Debromination proceeds in near quant. yield to give the targeted 3-methylcalix[4]arene-25,26,27,28-tetrol. 3-Methylcalix[4]arene undergoes reactions at the para position to give functionalized chiral calix[4]arenes in good to excellent yields. [on SciFinder(R)]