Volume 31, Issue 51
Preparative Organic Chemistry
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ChemInform Abstract: Neighboring Effect of Pyrazole Rings: Regio- and Stereoselective Wagner—Meerwein Rearrangement in Electrophilic Addition Reactions of Norbornadiene-Fused Pyrazoles.

Tomoshige Kobayashi

Tomoshige Kobayashi

Dep. Chem., Fac. Sci., Shinshu Univ., Asahi, Matsumoto 390, Japan

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Yosuke Ichiyama

Yosuke Ichiyama

Dep. Chem., Fac. Sci., Shinshu Univ., Asahi, Matsumoto 390, Japan

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First published: 31 May 2010

Abstract

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ChemInform Abstract

Fused pyrazoles (I) and (VII) undergo electrophilic addition of sulfenyl chloride (II) or bromine to afford skeletally rearranged adducts in a regio- and stereoselective manner which is attributable to the neighboring group participation of the pyrazole ring accompanied by the regioselective formation of a bridged pyrazolium ion.

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