Reactivities of stable rotamers. X. Reactions of 9-(2-formyl-1-naphthyl)fluorene rotamers and related compounds.
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Rotational barrier (<I>ap</I>→<I>sp</I>) in 9-(2-formyl-1-naphthyl)fluorene was determined: Δ<I>H</I><SUP>\neweq</SUP>24.0 kcal/mol and Δ<I>S</I><SUP>\neweq</SUP>−7.9 e.u. Oxidation of the aldehyde with chromium(VI) oxide was extremely slow in the <I>ap</I> form, whereas it proceeded smoothly in the <I>sp</I> form. As models of the 2 steps involved in the aldehyde oxidation, oxime formation of the aldehyde and oxidation of related alcohols were carried out to conclude that the second elimination step in the aldehyde oxidation is slow in the <I>ap</I> form because of the steric effect. Dehydration of the oxime of the aldehyde exhibited a large <I>k</I><SUB>sp</SUB>/<I>k</I><SUB>ap</SUB> value as well. Sodium tetrahydridoborate reduction and Grignard additions of the aldehyde were also carried out to show that the former gave a large <I>k</I><SUB>sp</SUB>/<I>k</I><SUB>ap</SUB> value whereas the latter exhibited rather a small <I>k</I><SUB>sp</SUB>/<I>k</I><SUB>ap</SUB>. The implication of the results is discussed.
- 公益社団法人 日本化学会の論文
著者
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Saito Ryo
Department Of Bioscience And Bioinformatics Faculty Of Computer Science And Systems Engineering Kyus
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Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
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