Nucleophilic substitution in 16π-antiaromatic system: Synthesis of heteroatom-substituted dibenzopentalenes

Feng Xu; Lifen Peng; Kan Wakamatsu; Akihiro Orita; Junzo Otera

doi:10.1246/cl.140583

Nucleophilic substitution in 16π-antiaromatic system: Synthesis of heteroatom-substituted dibenzopentalenes

Feng Xu
, Lifen Peng
, Kan Wakamatsu
, Akihiro Orita
, Junzo Otera

Chemistry (Twin Cities)

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

9 Scopus citations

Abstract

An antiaromatic compound, 5-bromo-10-iododibenzopentalene, underwent nucleophilic substitution of heteroatoms such as R₂NLi, ROLi, and RSLi. This subst itution proceeded preferentially at the bromopentalene moiety than at the iodo-counterpart. Combining this substitution and Sonogashira coupling enabled syntheses of π-systems expanded by a dibenzopentalene array and heteroatom(s).

Original language	English (US)
Article number	CL-140583
Pages (from-to)	1548-1550
Number of pages	3
Journal	Chemistry Letters
Volume	43
Issue number	10
DOIs	https://doi.org/10.1246/cl.140583
State	Published - 2014

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© 2014 The Chemical Society of Japan.

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10.1246/cl.140583

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abstract = "An antiaromatic compound, 5-bromo-10-iododibenzopentalene, underwent nucleophilic substitution of heteroatoms such as R2NLi, ROLi, and RSLi. This subst itution proceeded preferentially at the bromopentalene moiety than at the iodo-counterpart. Combining this substitution and Sonogashira coupling enabled syntheses of π-systems expanded by a dibenzopentalene array and heteroatom(s).",

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AU - Xu, Feng

AU - Peng, Lifen

AU - Wakamatsu, Kan

AU - Orita, Akihiro

AU - Otera, Junzo

PY - 2014

Y1 - 2014

N2 - An antiaromatic compound, 5-bromo-10-iododibenzopentalene, underwent nucleophilic substitution of heteroatoms such as R2NLi, ROLi, and RSLi. This subst itution proceeded preferentially at the bromopentalene moiety than at the iodo-counterpart. Combining this substitution and Sonogashira coupling enabled syntheses of π-systems expanded by a dibenzopentalene array and heteroatom(s).

AB - An antiaromatic compound, 5-bromo-10-iododibenzopentalene, underwent nucleophilic substitution of heteroatoms such as R2NLi, ROLi, and RSLi. This subst itution proceeded preferentially at the bromopentalene moiety than at the iodo-counterpart. Combining this substitution and Sonogashira coupling enabled syntheses of π-systems expanded by a dibenzopentalene array and heteroatom(s).

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ER -

Nucleophilic substitution in 16π-antiaromatic system: Synthesis of heteroatom-substituted dibenzopentalenes

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