Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units

W. Brad Wan; Ryan C. Chiechi; Timothy J.R. Weakley; Michael M. Haley

doi:10.1002/1099-0690(200109)2001:18<3485::AID-EJOC3485>3.0.CO;2-I

Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units

W. Brad Wan
, Ryan C. Chiechi
, Timothy J.R. Weakley
, Michael M. Haley

Stratingh Institute for Chemistry

Research output: Contribution to journal › Article › Academic

17 Citations (Scopus)

63 Downloads (Pure)

Abstract

Dehydrobenzoannulene derivatives containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.

Original language	English
Pages (from-to)	3485-3490
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2001
Issue number	18
DOIs	https://doi.org/10.1002/1099-0690(200109)2001:18<3485::AID-EJOC3485>3.0.CO;2-I
Publication status	Published - 2001

Keywords

Macrocycles
Cross-coupling
Aromaticity
Annulenes
Alkynes

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title = "Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units",

abstract = "Dehydrobenzoannulene derivatives containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.",

keywords = "Macrocycles, Cross-coupling, Aromaticity, Annulenes, Alkynes",

author = "Wan, \{W. Brad\} and Chiechi, \{Ryan C.\} and Weakley, \{Timothy J.R.\} and Haley, \{Michael M.\}",

note = "Relation: http://www.rug.nl/scheikunde/onderzoek/scholen/stratingh/index date\_submitted:2009 Rights: University of Groningen, Stratingh Institute for Chemistry",

year = "2001",

doi = "10.1002/1099-0690(200109)2001:18<3485::AID-EJOC3485>3.0.CO;2-I",

language = "English",

volume = "2001",

pages = "3485--3490",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "18",

}

TY - JOUR

T1 - Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units

AU - Wan, W. Brad

AU - Chiechi, Ryan C.

AU - Weakley, Timothy J.R.

AU - Haley, Michael M.

N1 - Relation: http://www.rug.nl/scheikunde/onderzoek/scholen/stratingh/index date_submitted:2009 Rights: University of Groningen, Stratingh Institute for Chemistry

PY - 2001

Y1 - 2001

N2 - Dehydrobenzoannulene derivatives containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.

AB - Dehydrobenzoannulene derivatives containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.

KW - Macrocycles

KW - Cross-coupling

KW - Aromaticity

KW - Annulenes

KW - Alkynes

U2 - 10.1002/1099-0690(200109)2001:18<3485::AID-EJOC3485>3.0.CO;2-I

DO - 10.1002/1099-0690(200109)2001:18<3485::AID-EJOC3485>3.0.CO;2-I

M3 - Article

SN - 1434-193X

VL - 2001

SP - 3485

EP - 3490

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 18

ER -

Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units

Abstract

Keywords

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