Synthesis of Hydroxysumanene and Substituent Effect of Hydroxy Group on Bowl Inversion Dynamics and Electronic Structure

Niti Ngamsomprasert, Gautam Panda, Shuhei Higashibayashi, Hidehiro Sakurai

研究成果: Article査読

13 被引用数 (Scopus)

抄録

Hydroxysumanene was synthesized from acylsumanenes by Baeyer-Villiger oxidation. DFT calculation predicted the higher bowl inversion energy and deeper bowl structure of hydroxysumanene than those of pristine sumanene. The bowl inversion energy of hydroxysumanene was experimentally determined by 2D-EXSY NMR measurement as 21.2 kcal/mol. The energy was larger than that of pristine sumanene (20.3 kcal/mol), which agreed with the calculation result. Electrochemical measurement indicated the higher HOMO level of hydroxysumanene than that of sumanene, which confirmed the electron-rich character of the phenolic function in the bowl skeleton.

本文言語English
ページ(範囲)11978-11981
ページ数4
ジャーナルJournal of Organic Chemistry
81
23
DOI
出版ステータスPublished - 2016 12月 2
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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