NDLI: Adding a Structural Context to the Deprotometalation and Trans-Metal Trapping Chemistry of Phenyl-Substituted Benzotriazole

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Adding a Structural Context to the Deprotometalation and Trans-Metal Trapping Chemistry of Phenyl-Substituted Benzotriazole

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Adding a Structural Context to the Deprotometalation and Trans-Metal Trapping Chemistry of Phenyl-Substituted Benzotriazole

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Rantanen, Toni Mulvey, Robert E. Parkinson, John A. Fuentes, M. Ángeles Kennedy, Alan R. Robertson, Stuart D. Snieckus, Victor
Description	Author Affiliation: Fuentes MÁ ( WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK), Fax: (+44) 141-548-4787.); Kennedy AR ( WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK), Fax: (+44) 141-548-4787.); Mulvey RE ( WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK), Fax: (+44) 141-548-4787. r.e.mulvey@strath.ac.uk.); Parkinson JA ( WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK), Fax: (+44) 141-548-4787.); Rantanen T ( Snieckus Innovations, Innovation Park, 945 Princess Street, Kingston, Ontario, K7L 3N6 (Canada).); Robertson SD ( WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL (UK), Fax: (+44) 141-548-4787.); Snieckus V ( Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, K7L 3N6 (Canada).)
Abstract	Organometallic bases are becoming increasingly complex, because mixing components can lead to bases superior to single-component bases. To better understand this superiority, it is useful to study metalated intermediate structures prior to quenching. This study is on 1-phenyl-1H-benzotriazole, which was previously deprotonated by an in situ $ZnCl_{2}⋅TMEDA/LiTMP$ (TMEDA=N,N,N′,N′-tetramethylethylenediamine; TMP=2,2,6,6-tetramethylpiperidide) mixture and then iodinated. Herein, reaction with LiTMP exposes the deficiency of the single-component base as the crystalline product obtained was $[\{4-R-1-(2-lithiophenyl)-1H-benzotriazole⋅3THF\}_{2}],$ $[R=2-C_{6}H_{4}(Ph)NLi],$ in which ring opening of benzotriazole and $N_{2}$ extrusion had occurred. Supporting lithiation by adding $iBu_{2}Al(TMP)$ induces trans-metal trapping, in which CLi bonds transform into CAl bonds to stabilise the metalated intermediate. X-ray diffraction studies revealed homodimeric $[(4-R′-1-phenyl-1H-benzotriazole)_{2}],$ $[R′=(iBu)_{2}Al(μ-TMP)Li],$ and its heterodimeric isomer [(4-R′-1-phenyl-1H-benzotriazole){2-R′-1-phenyl-1H-benzotriazole}], whose structure and slow conformational dynamics were probed by solution NMR spectroscopy.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	42
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-10-12
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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