Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 Fragment Sumanene

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 Wagner–Meerwein rearrangement of a five-membered ring to a six-membered one. Both theoretical and experimental investigations exhibited the shall...

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Veröffentlicht in:Chemistry letters 2017, Vol.46 (10), p.1556-1559
Hauptverfasser: Hishikawa, Shota, Okabe, Yuki, Tsuruoka, Ryoji, Higashibayashi, Shuhei, Ohtsu, Hiroyoshi, Kawano, Masaki, Yakiyama, Yumi, Sakurai, Hidehiro
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container_end_page 1559
container_issue 10
container_start_page 1556
container_title Chemistry letters
container_volume 46
creator Hishikawa, Shota
Okabe, Yuki
Tsuruoka, Ryoji
Higashibayashi, Shuhei
Ohtsu, Hiroyoshi
Kawano, Masaki
Yakiyama, Yumi
Sakurai, Hidehiro
description 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 Wagner–Meerwein 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.
doi_str_mv 10.1246/cl.170612
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source Oxford University Press Journals All Titles (1996-Current)
subjects Buckminsterfullerene
Chemical reactions
Fullerenes
Organic chemistry
Physical properties
title Synthesis of a C70 Fragment Buckybowl C28H14 from a C60 Fragment Sumanene
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