Volume 21, Issue 37
Isocyclic Compounds
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ChemInform Abstract: Transannular Deactivation in Tetrafluoro(2.2)paracyclophane. Electrophilic Reactivity of Its Open-Chain Analogue.

R. FILLER

R. FILLER

Dep. Chem., Ill. Inst. Technol., Chicago, IL 60616, USA

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J. E. GADOMSKI

J. E. GADOMSKI

Dep. Chem., Ill. Inst. Technol., Chicago, IL 60616, USA

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First published: September 11, 1990

Abstract

Acetylation of (IV), an open-chain analogue of 4,5,7,8-tetrafluoro-(2.2)paracyclophane (VII), proceeds in contrast to (VII) only at the phenyl ring.

ChemInform Abstract

Acetylation of (IV), an open-chain analogue of 4,5,7,8-tetrafluoro-(2.2)paracyclophane (VII), proceeds in contrast to (VII) only at the phenyl ring. This proves the suggestion that the inactivity of (VII) towards electrophilic reactions is due to transannular withdrawal of π-electron density from the phenyl ring.

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