Title | 3-Methylcalix[4]arene: A New Versatile Precursor to Inherently Chiral Calix[4]arenes. |
Publication Type | Journal Article |
Year of Publication | 1996 |
Authors | Fu, D-K, Xu, B, Swager, TM |
Journal | Journal of Organic Chemistry |
Volume | 61 |
Pagination | 802–804 |
ISSN | 0022-3263 |
Keywords | methylcalixarene prepn chiral calixarene, methylcalixarenetetrol prepn chiral calixarene |
Abstract | 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)] |
DOI | 10.1021/JO950929F |