Tetra-tert-butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour

TY - JOUR

T1 - Tetra-tert-butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour

AU - Brock-Nannestad, Theis

AU - Nielsen, Christian Benedikt

AU - Schau-Magnussen, Magnus

AU - Hammershøj, Peter

AU - Reenberg, Theis K.

AU - Petersen, Asger Bjørn

AU - Trpcevski, Denis

AU - Pittelkow, Michael

PY - 2011/11

Y1 - 2011/11

N2 - We describe the first example of the synthesis of a tetraoxa[8]circulene with only four substituents by means of BF3·OEt2 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.

AB - We describe the first example of the synthesis of a tetraoxa[8]circulene with only four substituents by means of BF3·OEt2 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.

M3 - Journal article

SN - 1434-193X

VL - 2011

SP - 6320

EP - 6325

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -