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

2 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

Fingerprint

Physical properties
sumanene

Keywords

  • C fragment buckybowl
  • Sumanene
  • Wagner-Meerwein rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hishikawa, S., Okabe, Y., Tsuruoka, R., Higashibayashi, S., Ohtsu, H., Kawano, M., ... 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

Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene. / Hishikawa, Shota; Okabe, Yuki; Tsuruoka, Ryoji; Higashibayashi, Shuhei; Ohtsu, Hiroyoshi; Kawano, Masaki; Yakiyama, Yumi; Sakurai, Hidehiro.

In: Chemistry Letters, Vol. 46, No. 10, 2017, p. 1556-1559.

Research output: Contribution to journalArticle

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, vol. 46, no. 10, pp. 1556-1559. https://doi.org/10.1246/cl.170612
Hishikawa, Shota ; Okabe, Yuki ; Tsuruoka, Ryoji ; Higashibayashi, Shuhei ; Ohtsu, Hiroyoshi ; Kawano, Masaki ; Yakiyama, Yumi ; Sakurai, Hidehiro. / Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene. In: Chemistry Letters. 2017 ; Vol. 46, No. 10. pp. 1556-1559.
@article{6185aeac486145228da4a899deeb0d8b,
title = "Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene",
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.",
keywords = "C fragment buckybowl, Sumanene, Wagner-Meerwein rearrangement",
author = "Shota Hishikawa and Yuki Okabe and Ryoji Tsuruoka and Shuhei Higashibayashi and Hiroyoshi Ohtsu and Masaki Kawano and Yumi Yakiyama and Hidehiro Sakurai",
year = "2017",
doi = "10.1246/cl.170612",
language = "English",
volume = "46",
pages = "1556--1559",
journal = "Chemistry Letters",
issn = "0366-7022",
publisher = "Chemical Society of Japan",
number = "10",

}

TY - JOUR

T1 - Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 fragment sumanene

AU - Hishikawa, Shota

AU - Okabe, Yuki

AU - Tsuruoka, Ryoji

AU - Higashibayashi, Shuhei

AU - Ohtsu, Hiroyoshi

AU - Kawano, Masaki

AU - Yakiyama, Yumi

AU - Sakurai, Hidehiro

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - C fragment buckybowl

KW - Sumanene

KW - Wagner-Meerwein rearrangement

UR - http://www.scopus.com/inward/record.url?scp=85032488296&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85032488296&partnerID=8YFLogxK

U2 - 10.1246/cl.170612

DO - 10.1246/cl.170612

M3 - Article

AN - SCOPUS:85032488296

VL - 46

SP - 1556

EP - 1559

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

IS - 10

ER -