Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones

Bao Jian Pei; Wing Hong Chan; Albert W.M. Lee

doi:10.1021/ol200309v

Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones

Bao Jian Pei
, Wing Hong Chan
, Albert W.M. Lee

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

27 Citations (Scopus)

Abstract

Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)₂/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.

Original language	English
Pages (from-to)	1774-1777
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	7
DOIs	https://doi.org/10.1021/ol200309v
Publication status	Published - 1 Apr 2011

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title = "Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones",

abstract = "Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)2/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.",

author = "Pei, \{Bao Jian\} and Chan, \{Wing Hong\} and Lee, \{Albert W.M.\}",

note = "Financial support from the Hong Kong Research Grants Council (HKBU 201307) is gratefully acknowledged. ",

year = "2011",

month = apr,

day = "1",

doi = "10.1021/ol200309v",

language = "English",

volume = "13",

pages = "1774--1777",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "7",

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TY - JOUR

T1 - Anthracene capped isobenzofuran

T2 - A synthon for the preparations of iptycenes and iptycene quinones

AU - Pei, Bao Jian

AU - Chan, Wing Hong

AU - Lee, Albert W.M.

N1 - Financial support from the Hong Kong Research Grants Council (HKBU 201307) is gratefully acknowledged.

PY - 2011/4/1

Y1 - 2011/4/1

N2 - Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)2/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.

AB - Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)2/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.

UR - https://www.scopus.com/pages/publications/79953200192

U2 - 10.1021/ol200309v

DO - 10.1021/ol200309v

M3 - Journal article

AN - SCOPUS:79953200192

SN - 1523-7060

VL - 13

SP - 1774

EP - 1777

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones

Abstract

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