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

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

Research output: Contribution to journalArticlepeer-review

7 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 languageEnglish (US)
Article numberCL-140583
Pages (from-to)1548-1550
Number of pages3
JournalChemistry Letters
Volume43
Issue number10
DOIs
StatePublished - 2014

Bibliographical note

Publisher Copyright:
© 2014 The Chemical Society of Japan.

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