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DISTAL Dibromoresorcin[4]arenes Through Selective Deactivation: A Practical Optimization
Author(s) -
Danielsiek Dominic,
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.202001031
Subject(s) - regioselectivity , chemistry , resorcinarene , steric effects , oligomer , yield (engineering) , limiting , cleavage (geology) , combinatorial chemistry , organic chemistry , catalysis , molecule , mechanical engineering , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
A simple and straightforward regioselective synthesis of distal disubstituted resorcin[4]arenes was developed, avoiding competing substitution patterns at an early stage via regioselective deactivation. Product limiting reaction steps were optimized by starting material recovery and by an improved protocol for ester cleavage while providing simple workup procedures throughout the synthesis without requiring column chromatography. The cyclizing acetalization of distal disubstituted resorcinarene octols proved to be a high yield process without oligomer formation, although less sterically controlled compared to the usual tetrabromo case.