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

Theis Brock-Nannestad; Christian Benedikt Nielsen; Magnus Schau-Magnussen; Peter Hammershøj; Theis K. Reenberg; Asger Bjørn Petersen; Denis Trpcevski; Michael Pittelkow

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

Theis Brock-Nannestad, Christian Benedikt Nielsen, Magnus Schau-Magnussen, Peter Hammershøj, Theis K. Reenberg, Asger Bjørn Petersen, Denis Trpcevski, Michael Pittelkow

Department of Chemistry

38 Citations (Scopus)

Abstract

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.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2011
Pages (from-to)	6320–6325
ISSN	1434-193X
Publication status	Published - Nov 2011

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title = "Tetra-tert-butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour",

abstract = "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.",

author = "Theis Brock-Nannestad and Nielsen, {Christian Benedikt} and Magnus Schau-Magnussen and Peter Hammersh{\o}j and Reenberg, {Theis K.} and Petersen, {Asger Bj{\o}rn} and Denis Trpcevski and Michael Pittelkow",

year = "2011",

month = nov,

language = "English",

volume = "2011",

pages = "6320–6325",

journal = "European Journal of Organic Chemistry",

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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 -

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

Abstract

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