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Konishi A, Minami Y, Hosoi T, et al. First Isolation and Characterization of the Highly Coordinated Group 14 Enolates: Effects of the Coordination Controls on the Geometry and Tautomerization of Germyl Enolates. Chemistry. 2016;22(36):12688-91doi: 10.1002/chem.201603147.
Konishi, A., Minami, Y., Hosoi, T., Chiba, K., & Yasuda, M. (2016). First Isolation and Characterization of the Highly Coordinated Group 14 Enolates: Effects of the Coordination Controls on the Geometry and Tautomerization of Germyl Enolates. Chemistry (Weinheim an der Bergstrasse, Germany), 22(36), 12688-91. https://doi.org/10.1002/chem.201603147
Konishi, Akihito, et al. "First Isolation and Characterization of the Highly Coordinated Group 14 Enolates: Effects of the Coordination Controls on the Geometry and Tautomerization of Germyl Enolates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,36 (2016): 12688-91. doi: https://doi.org/10.1002/chem.201603147
Konishi A, Minami Y, Hosoi T, Chiba K, Yasuda M. First Isolation and Characterization of the Highly Coordinated Group 14 Enolates: Effects of the Coordination Controls on the Geometry and Tautomerization of Germyl Enolates. Chemistry. 2016 Aug 26;22(36):12688-91. doi: 10.1002/chem.201603147. Epub 2016 Jul 28. PMID: 27377796.
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Chemistry. 2016 Aug 26;22(36):12688-91. doi: 10.1002/chem.201603147. Epub 2016 Jul 28.

First Isolation and Characterization of the Highly Coordinated Group 14 Enolates: Effects of the Coordination Controls on the Geometry and Tautomerization of Germyl Enolates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Akihito Konishi, Yohei Minami, Takahisa Hosoi, Kouji Chiba, Makoto Yasuda

Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.
  2. Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.
  3. Science and Technology System Division, Ryoka Systems Inc., Tokyo Skytree East Tower, 1-1-2 Oshiage, Sumida-ku, Tokyo, 131-0045, Japan.
  4. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan. [email protected].

PMID: 27377796 DOI: 10.1002/chem.201603147

Abstract

The Group 14 enolates play an important part in many organic reactions. Herein, the reduction of an α-bromo ketone with germanium(II) salts cleanly afforded the corresponding germyl enolate as an isolatable species. This experimental reductive generation of a germyl enolate enabled us to characterize both C- and O-bound tautomers derived from an identical precursor and to unveil the tautomeric mechanisms, including the kinetic parameters and the relative stability of these tautomers, along with confirmation from DFT calculations. Moreover, the highly coordinated germyl enolates were isolated by a stabilization process induced by adding ligands. All products were characterized by NMR spectroscopy and X-ray crystallography.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: germanium; germyl enolate; highly coordinated enolate; reaction order; tautomerization

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