Reactivities of stable rotamers. VI. Manifestation of differential reactivities of the methyls in a t-butyl group in radical halogenations.

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概要

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• The methyls in a <I>t</I>-butyl group are shown to exhibit different reactivities in radical halogenations, if rotation about a (CH<SUB>3</SUB>)<SUB>3</SUB>C–CXY<SUB>2</SUB> bond is frozen. Barriers to rotation of halogenated 9-<I>t</I>-butyl-1,2,3,4-tetrachlorotriptycenes are obtained as Δ<I>H</I><SUP>\neweq</SUP> <I>ca.</I> 32 kcal/mol. The cause of the selectivity in chlorination with sulfuryl chloride was discussed by obtaining reactivity data with a variety of compounds and halogenating reagents. It is concluded that the neighboring group participation of the peri-halo substituent is responsible for the observed selectivity.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Gaku

  Department Of Chemistry Faculty Of Science The University Of Tokyo

• Kikuchi Hiromi

  Department Of Applied Chemistry Graduate School Of Engineering Tohoku University

• Oki Michinori

  Department Of Chemistry Faculty Of Science Okawama University Of Science

• Kikuchi Hiromi

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Seki Shigetaka

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Morinaga Tsutou

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Mitsuhashi Tsutomu

  Department of Chemistry, Faculty of Science, The University of Tokyo

• MORINAGA Tsutou

  Department of Applied Chemistry, Faculty of Engineering, University of Tokyo

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