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

Niti Ngamsomprasert, Gautam Panda, Shuhei Higashibayashi, Hidehiro Sakurai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)11978-11981
Number of pages4
JournalJournal of Organic Chemistry
Volume81
Issue number23
DOIs
Publication statusPublished - 2016 Dec 2
Externally publishedYes

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this