Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene

The reaction of the diferrocenylphosphenium ion with four terminal allenes follows two different pathways, via allyl or vinyl carbocations, which proceed with electrophilic substitution reactions at one ferrocenyl moiety to form persistent Wheland intermediates and eventually alkenyldiferrocenylphosphonium salts. The reaction of the diferrocenylphosphenium ion with 2‐(trimethylsilyl)‐2,3‐pentadiene affords a stable Wheland intermediate of ferrocene in high yields, which is isolated and fully characterized.

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Publication Details

Journal
ChemistryEurope
Published
2025-05-23
DOI
https://doi.org/10.1002/ceur.202500031
Primary Topic
Ferrocene Chemistry and Applications
Type
article
Field-Weighted Citation Impact
0.00

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article

Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene

Jens Beckmann, Corina Stoian, Malte Fischer, Pim Puylaert et al.
ChemistryEurope
Ferrocene Chemistry and Applications
article

Activation of Allenes by Diferrocenylphosphenium Ion: Isolation of a Wheland Intermediate of Ferrocene

Jens Beckmann, Corina Stoian, Malte Fischer, Pim Puylaert, Emanuel Hupf, Serhiy Demeshko, Carolin Exner, Moritz Hornig
article en

Abstract

The reaction of the diferrocenylphosphenium ion with four terminal allenes follows two different pathways, via allyl or vinyl carbocations, which proceed with electrophilic substitution reactions at one ferrocenyl moiety to form persistent Wheland intermediates and eventually alkenyldiferrocenylphosphonium salts. The reaction of the diferrocenylphosphenium ion with 2‐(trimethylsilyl)‐2,3‐pentadiene affords a stable Wheland intermediate of ferrocene in high yields, which is isolated and fully characterized.

ChemistryEurope
University of Bremen (DE), University of Göttingen (DE)
Niedersächsische Ministerium für Wissenschaft und Kultur, Deutsche Forschungsgemeinschaft, Georg-August-Universität Göttingen
Openalex Percentile: Top 91%
Ferrocene Chemistry and Applications
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