Thermal transformation of ring-opened [2+2] C60 dimer into a wide-bridged C120 isomer. A computational evaluation of fulvalene-naphthalene rearrangements

Kazuhiko Honda, Eiji Osawa, Zdenek Slanina, Takatoshi Matsumoto

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18 Citations (Scopus)

Abstract

As a continuation of the studies on thermal transformation of the [2+2] C60 dimer (1), the consequence of the pyracylene-rearrangement-like valence isomerization of the fulvalene partial structure at the bridge of the ring-opened product from 1, namely 2, was searched by dynamic reaction coordinate /AM1 semiempirical MO calculations. It is predicted that the fulvalene bridge of 2 rearranges into naphthalene partial structure by the concerted 'in-plane' mechanism to give a wide-bridged C120 intermediate having twenty five-membered rings and two ten-membered rings (3). The computed energy of activation (145 kcal/mol) is 40 kcal/mol lower than those computed for pyracylene rearrangements. In contrast, the recently reported analogous rearrangement of indigo (13) to dibenzonaphthyridindione (14) is computed to occur by the stepwise 'sp3' mechanism.

Original languageEnglish
Pages (from-to)819-834
Number of pages16
JournalFullerene Science and Technology
Volume4
Issue number5
DOIs
Publication statusPublished - 1996

ASJC Scopus subject areas

  • Chemical Engineering(all)

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