Geometrical remote steric effects in 4,5-disubstituted-9,10- dihydrophenanthrenes: Expansion of prestrained C9-C10 bond in di(spiroacridan) derivatives

Kazuhisa Wada, Takashi Takeda, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    By attaching bulky substituents at the bay region of di(spiroacridan)- substituted dihydrophenanthrene 1a, the prestrained C9-C10 bond in the dihydrophenanthrene (DHP) skeleton of 1c-1e is expanded from 1.634(2) to 1.649(3)-1.652(6) Å, which demonstrates the bond expansion through remote steric effects. Twisting deformation of the DHP skeleton is the key to transfer the steric bulkiness from the C4/C5 positions to cause the additional strain in the C9-C10 bond.

    Original languageEnglish
    Pages (from-to)1194-1196
    Number of pages3
    JournalChemistry Letters
    Volume42
    Issue number10
    DOIs
    Publication statusPublished - 2013

    ASJC Scopus subject areas

    • Chemistry(all)

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