Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene

Shota Hishikawa, Yuki Okabe, Ryoji Tsuruoka, Shuhei Higashibayashi, Hiroyoshi Ohtsu, Masaki Kawano, Yumi Yakiyama, Hidehiro Sakurai

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A C70 fragment (1) (C28H14) was synthesized by conversion of a C60 fragment sumanene, via ring expansion and annulation in 3 steps, the key step being the WagnerMeerwein rearrangement of a five-membered ring to a six-membered one. Both theoretical and experimental investigations exhibited the shallower bowl structure of 1, resulting in the lower bowl inversion barrier than sumanene. It was also revealed that the indenopyrene skeleton largely contributed to the physical properties of 1.

Original languageEnglish
Pages (from-to)1556-1559
Number of pages4
JournalChemistry Letters
Volume46
Issue number10
DOIs
Publication statusPublished - 2017

Keywords

  • C fragment buckybowl
  • Sumanene
  • Wagner-Meerwein rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

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    Hishikawa, S., Okabe, Y., Tsuruoka, R., Higashibayashi, S., Ohtsu, H., Kawano, M., Yakiyama, Y., & Sakurai, H. (2017). Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene. Chemistry Letters, 46(10), 1556-1559. https://doi.org/10.1246/cl.170612