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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Encapsulating Inorganic Acetylene, HBNH, Using Flanking Coordinative Interactions.

Anindya K Swarnakar1, Christian Hering-Junghans1, Koichi Nagata2

  • 1Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta, T6G 2G2 (Canada) http://www.chem.ualberta.ca/∼erivard/

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|July 28, 2015
PubMed
Summary

Researchers created a stable complex of inorganic iminoborane (HBNH), an acetylene analogue. This breakthrough offers a new pathway for synthesizing unsaturated inorganic materials for advanced applications.

Keywords:
boroncarbenesdonor-acceptor systemsmultiple bondsnitrogen

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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Organometallic Chemistry

Background:

  • The parent inorganic iminoborane (HBNH) is a highly reactive and elusive species, analogous to acetylene.
  • Stable coordination complexes are crucial for studying and utilizing reactive inorganic species.

Purpose of the Study:

  • To synthesize and characterize a stable donor-acceptor coordination complex of the parent inorganic iminoborane (HBNH).
  • To investigate the mechanism of HBNH formation from a hydrido(azido)borane adduct.
  • To establish a new synthetic route to unsaturated inorganic building blocks.

Main Methods:

  • Thermal decomposition of a hydrido(azido)borane adduct (NHC⋅BH2N3) in the presence of a fluorinated triarylborane.
  • Spectroscopic characterization of the resulting coordination complex.
  • Computational studies and isotopic labeling to elucidate the reaction mechanism.

Main Results:

  • A stable donor-acceptor coordination complex of HBNH was successfully synthesized and characterized.
  • The formation of HBNH was achieved via thermally induced N2 elimination and 1,2-H migration.
  • The reaction mechanism was confirmed through computational modeling and isotopic labeling experiments.

Conclusions:

  • This work reports the first stable coordination complex of the parent inorganic iminoborane (HBNH).
  • The developed method provides a novel and potentially modular route for accessing unsaturated inorganic compounds.
  • These findings open avenues for the synthesis of advanced materials utilizing HBNH as a building block.