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Facile Preparation of [4.4]Metacyclophane‐ and [5.5]Paracyclophane‐Type Macrocycles from Arylboronic Acids and Salicylideneaminoaryl Alcohols
Author(s) -
Sánchez Mario,
Höpfl Herbert,
Ochoa MariaEugenia,
Farfán Norberto,
Santillan Rosa,
RojasLima Susana
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020201)8:3<612::aid-chem612>3.0.co;2-4
Subject(s) - boron , intramolecular force , cyclophane , chemistry , monomer , hydrogen bond , yield (engineering) , polymer chemistry , stereochemistry , molecule , organic chemistry , materials science , polymer , metallurgy
Four different salicylideneaminoaryl alcohols have been treated with arylboronic acids in order to prepare air‐stable cyclophane‐type macrocyclic systems. In two cases, this objective could be realized with the high‐yield formation of [4.4]metacyclophane and [5.5]paracyclophane derivatives. The skeleton in these macrocycles is held together by two chiral boron atoms. In the other two cases, monomeric boronates or polymeric material were obtained. The title structures were characterized by spectroscopic techniques and X‐ray crystallography. They show transannular C−H⋅⋅⋅O hydrogen bonding, but no intramolecular π–π interactions. A synthetic strategy for the preparation of further boron macrocycles is presented.