Selective Halogen−Lithium Exchange Reaction of Bromine-Substituted 25,26,27,28-Tetrapropoxycalix[4]arene
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (19) , 6651-6655
- https://doi.org/10.1021/jo9609440
Abstract
Methods are described for the selective bromine-lithium exchange reaction of bromine-substituted calix[4]arenes with either n-BuLi or t-BuLi in THF. Quenching of the lithiated calix[4]arenes with MeOH, D(2)O, CH(3)SSCH(3), B(OCH(3))(3), DMF, or CO(2) as electrophiles resulted in 5-monosubstituted, 5,17-disubstituted, or 5,11,17,23-tetrasubstituted calix[4]arenes with H, D, SCH(3), B(OH)(2), CHO, or COOH functionalities.Keywords
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