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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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5-Methyl-2-thienylcalcium iodide.

Alexander Koch1, Sven Krieck, Helmar Görls

  • 1Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 8, D-07743 Jena, Germany. m.we@uni-jena.de.

Dalton Transactions (Cambridge, England : 2003)
|May 5, 2018
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This summary is machine-generated.

Synthesizing thienylcalcium halides, essential heavy Grignard reagents, was challenging. New methods using calcium-iodine exchange and activated calcium enable their successful preparation and isolation for further chemical applications.

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Area of Science:

  • Organometallic Chemistry
  • Calcium Chemistry
  • Heterocyclic Chemistry

Background:

  • Direct reduction of bromothiophenes with calcium powder yields impure thienylcalcium complexes.
  • Side reactions like metalation, calcium-halogen exchange, and ether degradation complicate synthesis.

Purpose of the Study:

  • To develop reliable methods for synthesizing pure thienylcalcium halide complexes.
  • To investigate the formation and characterization of these organocalcium compounds.

Main Methods:

  • Calcium-iodine exchange using trimethylsilylmethylcalcium halide and 3-iodothiophene in tetrahydrofuran (THF) at -78 °C.
  • Reduction of 2-iodo-5-methylthiophene with activated calcium in THF to form thienylcalcium halide.
  • Ligand substitution of THF by tetrahydropyran (THP) in isolated complexes.

Main Results:

  • Quantitative formation of 3-(trimethylsilyl)thiophene achieved via calcium-iodine exchange.
  • Successful synthesis and isolation of 5-methyl-2-thienylcalcium iodide complexes with THF and THP ligands.
  • Characterization of thienylcalcium complexes by a characteristic low field shift of the calcium-bound carbon atom.

Conclusions:

  • Thienylcalcium halides can be synthesized and isolated using specific calcium-iodine exchange or reduction methods.
  • Ligand environment influences the properties of thienylcalcium complexes.
  • These organocalcium reagents offer potential as heavy Grignard analogues in organic synthesis.