Manifestation of Dual Aromaticity in Doubly Charged Annelated Pentalenes

Willner Itamar, James Y. Becker, Rabinovitz Mordecai*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

1,9-Dimethyldibenzo[b,f] pentalene (18) was oxidized and reduced chemically and electrochemically to the respective dication and dianion. The parent hydrocarbon dibenzo[b,f] pentalene (17) also formed the respective dication and dianion. The dication and dianion showed aromatic diatropicity. The NMR characteristics are discussed in terms of the aromaticity vs. charge effects and the validity of the peripheral model is presented. The electrochemical parameters are discussed in relation to the electronic character of these systems.

Original languageEnglish
Pages (from-to)395-401
Number of pages7
JournalJournal of the American Chemical Society
Volume101
Issue number2
DOIs
StatePublished - 1 Feb 1979

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