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Mono‐ and Tri‐Functionalization of Trimethylresorcin[4]arenes
Author(s) -
Loose Dirk,
Aniol Alexandra,
Feigel Martin,
Röhling Sebastian,
Dyker Gerald
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901564
Subject(s) - halogenation , chemistry , iodide , surface modification , resorcinol , bromide , tris , aryl , organic chemistry , condensation , combinatorial chemistry , medicinal chemistry , alkyl , biochemistry , physics , thermodynamics
Short and efficient syntheses of mono‐ and tris‐functionalized resorcin[4]arenes were developed. The co‐condensation of resorcinol and 2‐methylresorcinol was optimized, targeting for the trimethylresorcin[4]arene, easy to isolate. Complementary regiospecific conditions for the mono‐ and tris‐halogenation in almost quantitative yields are setting the stage for subsequent functionalizations: radicalic bromination leads to the trisbromomethyl compound, while the polar bromination and iodination via the mono‐lithiated species leads to the aryl bromide and iodide in excellent yields.