The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1] benzopyran

Christopher D. Gabbutt, B. Mark Heron, Colin Kilner, Suresh B. Kolla

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3 Citations (Scopus)

Abstract

The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1] benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected.

LanguageEnglish
Pages825-830
Number of pages6
JournalDyes and Pigments
Volume92
Issue number2
DOIs
Publication statusPublished - 1 Feb 2012
Externally publishedYes

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Photochromism
Benzopyrans
Palladium
Isomerization
Styrene
Condensation
Ligands
Pyrans
Stilbenes

Cite this

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title = "The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1] benzopyran",
abstract = "The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1] benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected.",
keywords = "Benzofuran, Benzopyran, Heck reaction, Hydroxystilbene, Photochromism, Ring-contraction",
author = "Gabbutt, {Christopher D.} and Heron, {B. Mark} and Colin Kilner and Kolla, {Suresh B.}",
year = "2012",
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doi = "10.1016/j.dyepig.2011.05.005",
language = "English",
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pages = "825--830",
journal = "Dyes and Pigments",
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TY - JOUR

T1 - The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran

T2 - Dyes and Pigments

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Kilner, Colin

AU - Kolla, Suresh B.

PY - 2012/2/1

Y1 - 2012/2/1

N2 - The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1] benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected.

AB - The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1] benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected.

KW - Benzofuran

KW - Benzopyran

KW - Heck reaction

KW - Hydroxystilbene

KW - Photochromism

KW - Ring-contraction

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U2 - 10.1016/j.dyepig.2011.05.005

DO - 10.1016/j.dyepig.2011.05.005

M3 - Article

VL - 92

SP - 825

EP - 830

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

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