NDLI: S-Alkylation of Soft Scorpionates

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S-Alkylation of Soft Scorpionates

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S-Alkylation of Soft Scorpionates

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Reglinski, John Diamond, Louise M. Moore, Dean Spicer, Mark D. Rajasekharan-nair, Rajeev Darby, Lisa Chalmers, Kirsten Armstrong, David R. Wallace, Dawn
Description	Author Affiliation: Rajasekharan-Nair R ( WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.)
Abstract	The alkylation reactions of soft scorpionates are reported. The hydrotris(S-alkyl-methimazolyl)borate dications (alkyl=methyl, allyl, benzyl), which were prepared by the reaction of $Tm^{Me}$ anion and primary alkyl halides, have been isolated and structurally characterised. The reaction is, however, not universally successful. DFT analysis of these alkylation reactions (CS versus BH alkylation) indicates that the observed outcome is driven by kinetic factors. Extending the study to incorporate alternative imine thiones (mercaptobenzothiazole, bz; thiazoline, tz) led to the structural characterisation of di[aquo-μ-aquohydrotris(mercaptobenzothiazolyl)boratosodium], which contains sodium atoms in the $κ^{3}-S,S,S$ coordination mode. Alkylation of Na[Tbz] and Na[tzTtz] leads to decomposition resulting in the formation of the simple S-alkylated heterocycles. The analysis of the species involved in these reactions shows an inherent weakness in the BN bond in soft scorpionates, which has implications for their use in more advanced chemistry.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	7
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-02-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Alkylating Agents Chemistry Borates Thiones Alkylation Kinetics Molecular Structure
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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