Conformations and restricted rotation about amide C-N bonds of 2,2-dichloro-1'-formyl-3',4'-dihydrospiro(cyclopropane-1,2'(1'H)-quinoline) and related compounds.

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概要

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• Conformational preference and rotational barriers of 1′,1′,2,2-tetrachloro-3′-formyl-1′a,7′b-dihydrospiro[cyclopropane-1,2′(3′<I>H</I>)-cyclopropa[<I>c</I>]quinolines] (<B>1</B>) and related <I>N</I>-formyl heterocyclic compounds were determined by <SUP>1</SUP>H- and <SUP>13</SUP>C-NMR spectroscopy. The <I>sp</I>-conformer is usually more preferable in <B>1</B> and their rotational barriers about amide C–N bond are within a relatively narrow range from 70.7 to 72.8 kJ mol<SUP>−1</SUP>. Infrared carbonyl absorptions of these compounds also support the preferred conformation from the NMR data. The results were discussed from the view point of N–C=O conjugation.

• 公益社団法人 日本化学会の論文

著者

• SUGIURA Michiharu

  Faculty of Pharmacy, Meijo University

• HAMADA Yoshiki

  Faculty of Pharmacy, Meijo University

• Hirota Minoru

  Department Of Animal Science Obihiro University Of Agriculture And Veterinary Medicine

• Suezawa (née

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

• Hirota Minoru

  Deparment of Synthetic Chemistry, Division of Materials Science and Chemical Engineering, Faculty of Engineering, Yokohama National University

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