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Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes via a ‘sulfur approach’


Mloston, Grzegorz; Hamera-Faldyga, Roza; Celeda, Malgorzata; Heimgartner, Heinz (2018). Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes via a ‘sulfur approach’. Organic & Biomolecular Chemistry, 16(23):4350-4356.

Abstract

Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the ‘two-fold extrusion’ reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.

Abstract

Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the ‘two-fold extrusion’ reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry
Language:English
Date:June 2018
Deposited On:07 Jun 2018 07:33
Last Modified:19 Aug 2018 15:54
Publisher:Royal Society of Chemistry
ISSN:1477-0520
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/c8ob01022f
PubMed ID:29850725
Project Information:
  • : FunderNational Science Center, Cracow
  • : Grant IDMaestro-3, grant no. Dec-2012/06/A/ST5/00219
  • : Project Title
  • : FunderAlexander von Humboldt Foundation Bonn
  • : Grant ID
  • : Project Title

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