Item type:Thesis, Open Access

Synthesis, Properties and Reactivity of Functional Carbodiphosphoranes (CDPs): From Cyclic to P-Cyclopentadienyl and P-Imidazolyl Substituted CDPs

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2025-12-10

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Abstract

The present Thesis expands our knowledge about P-functionalized carbodiphosphoranes (CDPs), a class of phosphorus ylides displaying two highly basic and nucleophilic electron lone pairs at the central carbon atom. They are called carbones in contrast to carbenes, their one-lone-pair counterparts. First Chapter is devoted to the isolation of new cyclic CDPs, referred to as CCDPs. In literature, only a few CCDPs have been described, predominantly with a more flexible aliphatic backbone compatible with a rather flexible central P=C=P unit. Six-, seven- and eight-membered cyclic carbodiphosphoranes (CCDPs) with conjugated aromatic backbones were synthesized from a route originally developed by Schmidbaur for non-cyclic CDPs. Their reactivity was studied with several metal complexes. Second Chapter is devoted to the synthesis of functionalized derivatives of classical hexaphenyl carbodiphosphorane, where one or two phenyl substituents are formally replaced by aromatic cyclopentadienyl anions. Reversible C-C bond formation was observed in presence of an acid and a base. This success in P-functionalization encouraged investigations described in third Chapter of this Thesis. Starting from previously described Cl2CDP, bis N-imidazolyl substituted Im2CDP, bis N-benzimidazolyl Bzi2CDP and bis N-perimidinyl substituted Perimid2CDP were synthesized via reaction with N-potassium nucleophiles.

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Dates
Issued: 2025-12-10
Faculty
FB15:Chemie
Language
en
Keywords
Chemistry
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Attribution-NonCommercial-NoDerivs 3.0 Germany
URI
https://open.uni-marburg.de/handle/openumr/9579
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Pal, Subhankar: Synthesis, Properties and Reactivity of Functional Carbodiphosphoranes (CDPs): From Cyclic to P-Cyclopentadienyl and P-Imidazolyl Substituted CDPs. : 2025-12-10.

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Attribution-NonCommercial-NoDerivs 3.0 Germany
Except where otherwised noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Germany