The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Lyndsey M. Greig; Alexandra M.Z. Slawin; Melanja H. Smith; Douglas Philp

doi:10.1016/j.tet.2006.12.034

The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Lyndsey M. Greig, Alexandra M.Z. Slawin, Melanja H. Smith, Douglas Philp^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound.

Original language	English (US)
Pages (from-to)	2391-2403
Number of pages	13
Journal	Tetrahedron
Volume	63
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2006.12.034
State	Published - Mar 12 2007

Keywords

Aromatic compounds
Dynamic covalent chemistry
Molecular recognition
Reversible reactions
Self-assembly

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.12.034

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title = "The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics",

abstract = "10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound.",

keywords = "Aromatic compounds, Dynamic covalent chemistry, Molecular recognition, Reversible reactions, Self-assembly",

author = "Greig, {Lyndsey M.} and Slawin, {Alexandra M.Z.} and Smith, {Melanja H.} and Douglas Philp",

note = "Funding Information: We thank the Engineering and Physical Science Research Council and the University of St Andrews for financial support of this work. ",

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AU - Greig, Lyndsey M.

AU - Slawin, Alexandra M.Z.

AU - Smith, Melanja H.

AU - Philp, Douglas

N1 - Funding Information: We thank the Engineering and Physical Science Research Council and the University of St Andrews for financial support of this work.

PY - 2007/3/12

Y1 - 2007/3/12

N2 - 10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound.

AB - 10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound.

KW - Aromatic compounds

KW - Dynamic covalent chemistry

KW - Molecular recognition

KW - Reversible reactions

KW - Self-assembly

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EP - 2403

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Abstract

Keywords

ASJC Scopus subject areas

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