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Facile dissociation of BS coordination bonds in [2,6-bis(ethylthiomethyl)phenyl]diethylborane by an S_N2-type mechanism

Corresponding Author

Shinji Toyota

[email protected]

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, JapanSearch for more papers by this author

Nobuhide Uemitsu,

Nobuhide Uemitsu

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

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Michinori Ōki,

Michinori Ōki

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

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Shinji Toyota,

Corresponding Author

Shinji Toyota

[email protected]

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, JapanSearch for more papers by this author

Nobuhide Uemitsu,

Nobuhide Uemitsu

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

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Michinori Ōki,

Michinori Ōki

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700–0005, Japan

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First published: 15 April 2004

https://doi.org/10.1002/hc.20005

Citations: 4

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Abstract

The title organoboron complex undergoes dissociation of the intramolecular B–S coordination bond much faster than the corresponding mono ethylthiomethyl complex as revealed by the dynamic NMR study. The facile dissociation is attributable to an S_N2-type mechanism, where the uncoordinated ligand assists the dissociation of the coordinated ligand in the transition state. This mechanism is supported by the initio calculations of a model reaction system. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:241–245, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20005

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Facile dissociation of BS coordination bonds in [2,6-bis(ethylthiomethyl)phenyl]diethylborane by an S_N2-type mechanism

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Facile dissociation of BS coordination bonds in [2,6-bis(ethylthiomethyl)phenyl]diethylborane by an SN2-type mechanism

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Facile dissociation of BS coordination bonds in [2,6-bis(ethylthiomethyl)phenyl]diethylborane by an S_N2-type mechanism