Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes

Feng Xu, Lifen Peng, Kenta Shinohara, Takamoto Morita, Suguru Yoshida, Takamitsu Hosoya, Akihiro Orita, Junzo Otera

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.

Original languageEnglish (US)
Pages (from-to)11592-11608
Number of pages17
JournalJournal of Organic Chemistry
Volume79
Issue number23
DOIs
StatePublished - Dec 5 2014

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