Superelectrophilic Cyclizations Involving 2-Norbornyl Dications

A series of anilino 2-norbornyl alcohols have been prepared and reacted in strongly acidic media. The chemistry provides ring-fused norbornane products in good yields (12 examples, 81-99% yields). A mechanism is proposed involving a novel ammonium-carbonium dicationic intermediate.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-13
DOI
https://doi.org/10.1021/acs.joc.5c01982
Primary Topic
Organic and Inorganic Chemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Superelectrophilic Cyclizations Involving 2-Norbornyl Dications

Douglas A. Klumpp, Milan Gembický, Grant P. Holmin
The Journal of Organic Chemistry
Organic and Inorganic Chemical Reactions
article

Superelectrophilic Cyclizations Involving 2-Norbornyl Dications

Douglas A. Klumpp, Milan Gembický, Grant P. Holmin
article en

Abstract

A series of anilino 2-norbornyl alcohols have been prepared and reacted in strongly acidic media. The chemistry provides ring-fused norbornane products in good yields (12 examples, 81-99% yields). A mechanism is proposed involving a novel ammonium-carbonium dicationic intermediate.

The Journal of Organic ChemistryVol. 90(42)
Northern Illinois University (US), University of California San Diego (US)
Openalex Percentile: Top 73%
Organic and Inorganic Chemical Reactions
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