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Tetra‐ tert ‐butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour
Author(s) -
BrockNannestad Theis,
Nielsen Christian B.,
SchauMagnussen Magnus,
Hammershøj Peter,
Reenberg Theis K.,
Petersen Asger B.,
Trpcevski Denis,
Pittelkow Michael
Publication year - 2011
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.201100966
Subject(s) - tetra , chemistry , stereochemistry , structural isomer , crystal structure , polymerization , medicinal chemistry , crystallography , organic chemistry , polymer
We describe the first example of the synthesis of a tetraoxa[8]circulene with only four substituents by means of BF 3 · OEt 2 mediated tetramerisation of tert ‐butyl‐1,4‐benzoquinone. Two of the four regioisomers of tetra‐ tert ‐butyltetraoxa[8]circulene have been isolated and characterised by single‐crystal X‐ray analysis. It was found that the tetra‐ tert ‐butyltetraoxa[8]circulenes aggregate in solution through a cooperative polymerisation mechanism despite functionalisation with bulky tert ‐butyl substituents.