A Rationale for the Ortho Effect in Electrophilic Aromatic Substitutions

Author(s): Timothy Eckert*, Grace Harmeyer, Steven Legate, Steven Mathe

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 9 , 2020


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Abstract:

The ortho effect arises in certain electrophilic aromatic substitutions when a meta director is meta to an ortho/para director. Among the three expected isomer products, only the two isomers ortho to the meta director are produced normally. To find an explanation for the ortho effect, nitrations of two properly substituted benzenes were explored. Evidence supported an explanation based on resonance involving the meta director.

Keywords: Electrophilic aromatic substitutions, ortho effect, resonance, nitration, directing groups, meta director.

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Holleman, A.F. Die direkte Einführung von Substituenten in den Benzolkern, 1st ed; Verlag: Veit, Leipzig 1910.
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Article Details

VOLUME: 17
ISSUE: 9
Year: 2020
Published on: 16 September, 2020
Page: [655 - 658]
Pages: 4
DOI: 10.2174/1570178617666200207103755
Price: $65

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