Induced Correspondence of a Local π-Aromatic Sextet in Heteroannulenes: Synthesis and Characterization

Abhijit Mallick; Juwon Oh; Dongho Kim; Masatoshi Ishida; Hiroyuki Furuta; Harapriya Rath

doi:10.1002/chem.201600380

Induced Correspondence of a Local π-Aromatic Sextet in Heteroannulenes: Synthesis and Characterization

Abhijit Mallick
, Juwon Oh
, Dongho Kim
, Masatoshi Ishida
, Hiroyuki Furuta
, Harapriya Rath

Department of Chemistry

Indian Association for the Cultivation of Science
Yonsei University
Kyushu University

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

8 Scopus citations

Abstract

Acid-catalyzed [3+3] condensation reactions of two hitherto unknown tripyrrane moieties with pentafluorobenzaldehyde has led to the formation of new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π-aromatic sextets, namely the N-methyl pyrrole rings through β,β-linkages and α,β-linkages, has led to the isolation of first ever heteroannulenes cross-conjugated at four points and two points respectively within the macrocycles.

Original language	English
Pages (from-to)	5504-5508
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	16
DOIs	https://doi.org/10.1002/chem.201600380
State	Published - 11 Apr 2016

Keywords

aromaticity
cross-conjugation
heteroannulenes
unconventional pyrrole connectivity
unorthodox tripyrranes

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10.1002/chem.201600380

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title = "Induced Correspondence of a Local π-Aromatic Sextet in Heteroannulenes: Synthesis and Characterization",

abstract = "Acid-catalyzed [3+3] condensation reactions of two hitherto unknown tripyrrane moieties with pentafluorobenzaldehyde has led to the formation of new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π-aromatic sextets, namely the N-methyl pyrrole rings through β,β-linkages and α,β-linkages, has led to the isolation of first ever heteroannulenes cross-conjugated at four points and two points respectively within the macrocycles.",

keywords = "aromaticity, cross-conjugation, heteroannulenes, unconventional pyrrole connectivity, unorthodox tripyrranes",

author = "Abhijit Mallick and Juwon Oh and Dongho Kim and Masatoshi Ishida and Hiroyuki Furuta and Harapriya Rath",

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T1 - Induced Correspondence of a Local π-Aromatic Sextet in Heteroannulenes

T2 - Synthesis and Characterization

AU - Mallick, Abhijit

AU - Oh, Juwon

AU - Kim, Dongho

AU - Ishida, Masatoshi

AU - Furuta, Hiroyuki

AU - Rath, Harapriya

PY - 2016/4/11

Y1 - 2016/4/11

N2 - Acid-catalyzed [3+3] condensation reactions of two hitherto unknown tripyrrane moieties with pentafluorobenzaldehyde has led to the formation of new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π-aromatic sextets, namely the N-methyl pyrrole rings through β,β-linkages and α,β-linkages, has led to the isolation of first ever heteroannulenes cross-conjugated at four points and two points respectively within the macrocycles.

AB - Acid-catalyzed [3+3] condensation reactions of two hitherto unknown tripyrrane moieties with pentafluorobenzaldehyde has led to the formation of new generation heteroannulene (4.1.4.1) and mutant heteroannulene (1.1.1.1.1.1). Inclusion of local π-aromatic sextets, namely the N-methyl pyrrole rings through β,β-linkages and α,β-linkages, has led to the isolation of first ever heteroannulenes cross-conjugated at four points and two points respectively within the macrocycles.

KW - aromaticity

KW - cross-conjugation

KW - heteroannulenes

KW - unconventional pyrrole connectivity

KW - unorthodox tripyrranes

UR - https://www.scopus.com/pages/publications/84960153936

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DO - 10.1002/chem.201600380

M3 - Article

AN - SCOPUS:84960153936

SN - 0947-6539

VL - 22

SP - 5504

EP - 5508

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 16

ER -

Induced Correspondence of a Local π-Aromatic Sextet in Heteroannulenes: Synthesis and Characterization

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Keywords

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