Substituent effects for the benzene ring on solvolysis of 3,4-benzo-tricyelo(4.3.1.01,6)dec-3-en-2-yl p-nitrobenzoate.

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概要

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• Preparations of <I>anti</I>-4′-substituted 3,4-benzotricyclo[4. 3. 1. 0<SUP>1,6</SUP>]dec-3-en-2-yl <I>p</I>-nitrobenzoates (<B>1a</B>–<B>d</B>) are described. The solvolysis of these esters was examined in 80% aqueous acetone. The rates were relatively high but the sensitivity to substituents on the benzene ring was low in comparison with other secondary systems. It is considered that σ-participation rather than π-conjugation might contribute to the rate accelerative effect. In the presence of a base, <B>1a</B>–<B>d</B> gave <I>anti</I>-alcohol (<B>12a</B>–<B>d</B>) (13 to 17%), <I>syn</I>-alcohol (<B>13a</B>–<B>d</B>) (31 to 78%), and <I>tert</I>-alcohol (<B>14a</B>–<B>d</B>) (5 to 54%). The product distributions are explained in terms of a nonclassical homonaphthalenium cation (<B>24</B>).

• 公益社団法人 日本化学会の論文

著者

• Ohkata Katsuo

  Chemistry Department, Faculty of Science, Hiroshima University

関連論文

• Solvolysis of 2,3-cyclopenteno-4H-homochromen-4-ol acetate: comparison with the corresponding carbocylic system.
• Substituent effects for the benzene ring on solvolysis of 3,4-benzo-tricyelo(4.3.1.01,6)dec-3-en-2-yl p-nitrobenzoate.

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