On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

Virginia Mazzanti; Martina Cacciarini; Søren Lindbæk Broman; Christian Richard Parker; Magnus Schau-Magnussen; Andrew Bond; Mogens Brøndsted Nielsen

doi:10.3762/bjoc.8.108

On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

Virginia Mazzanti, Martina Cacciarini, Søren Lindbæk Broman, Christian Richard Parker, Magnus Schau-Magnussen, Andrew Bond, Mogens Brøndsted Nielsen

Department of Chemistry

16 Citations (Scopus)

Abstract

Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	8
Pages (from-to)	958–966
Number of pages	9
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.8.108
Publication status	Published - 27 Jun 2012

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title = "On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch",

abstract = "Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.",

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year = "2012",

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doi = "10.3762/bjoc.8.108",

language = "English",

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T1 - On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

AU - Mazzanti, Virginia

AU - Cacciarini, Martina

AU - Broman, Søren Lindbæk

AU - Parker, Christian Richard

AU - Schau-Magnussen, Magnus

AU - Bond, Andrew

AU - Nielsen, Mogens Brøndsted

PY - 2012/6/27

Y1 - 2012/6/27

N2 - Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.

AB - Background: The dihydroazulene (DHA)/vinylheptafulvene (VHF) system (with two cyano groups at C1) functions as a photo-/thermoswitch. Direct ionic bromination of DHA has previously furnished a regioselective route to a 7,8-dibromide, which by elimination was converted to a 7-bromo-substituted DHA. This compound has served as a central building block for functionalization of the DHA by palladium-catalyzed cross-coupling reactions. The current work explores another bromination protocol for achieving the isomeric 3-bromo-DHA and also explores the outcome of additional bromination of this compound as well as of the known 7-bromo-DHA.

U2 - 10.3762/bjoc.8.108

DO - 10.3762/bjoc.8.108

M3 - Journal article

C2 - 23015846

SN - 2195-951X

VL - 8

SP - 958

EP - 966

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

On the bromination of the dihydroazulene/vinylheptafulvene photo-/thermoswitch

Abstract

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