Improved methods for the halogenation of the [HCB11H11]− anion

Gu, Weixing; McCulloch, Billy J.; Reibenspies, Joseph H.; Ozerov, Oleg V.

doi:10.1039/c001555e

Cited by 45 publications

(43 citation statements)

References 29 publications

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“…The [Ph 3 C] + cation shows also no significant interactions with the solvate molecules. The sum of the angles around C1 is 360.0(4)° which is expected for a free trityl cation and is also observed in crystal structures of the [Ph 3 C] + cation with other weakly coordinating anions ([B 12 Cl 12 ] 2− ,11 [Me 3 NB 12 F 11 ] − ,12 [1‐H‐CB 11 Br 11 ]14). …”

Section: Resultssupporting

confidence: 63%

“…Similar reaction conditions were used by Ozerov et al. for the perchlorination of the [1‐H‐CB 11 H 11 ] − anion 14. Attempts to fully chlorinate the [H 3 NB 12 H 11 ] − anion using other chlorinating agents (for example, Cl 2 in boiling water or acetic acid; SO 2 Cl 2 in boiling acetonitrile) only led to mixtures of partly chlorinated clusters.…”

Section: Resultsmentioning

confidence: 86%

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Synthesis and Properties of the Weakly Coordinating Anion [Me₃NB₁₂Cl₁₁]⁻

Bolli

Derendorf

Jenne

et al. 2014

Chemistry A European J

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The weakly coordinating anion [Me3 NB12 Cl11 ](-) has been prepared by a simple two-step procedure. The anion [Me3 NB12 Cl11 ](-) is easily obtained in batches of up to 20 g by chlorination of the known [H3 NB12 H11 ](-) anion with SbCl5 at about 190 °C and subsequent N-methylation with methyl iodide. Starting from Na[Me3 NB12 Cl11 ], several synthetically useful salts with reactive cations ([NO](+) , [Ph3 C](+) , and [(Et3 Si)2 H](+) ) were prepared. Full spectroscopic (NMR, IR, Raman, TGA, MS) characterization and single-crystal X-ray diffraction studies confirmed the identity and purity of the products. The thermal, chemical, and electrochemical stability as well as the basicity of the [Me3 NB12 Cl11 ](-) anion is similar to that of the structurally related weakly coordinating 1-carba-closo-dodecaborate and closo-dodecaborate anions. The facile preparation of the [Me3 NB12 Cl11 ](-) anion and its ideal chemical and physical properties make it a cheap alternative to other classes of weakly coordinating anions.

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Section: Resultssupporting

confidence: 63%

Section: Resultsmentioning

confidence: 86%

Synthesis and Properties of the Weakly Coordinating Anion [Me₃NB₁₂Cl₁₁]⁻

Bolli

Derendorf

Jenne

et al. 2014

Chemistry A European J

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“…[Ph 3 C] [514] ; R = Me, X = F: [Ph 3 C] [98] ; R = Et X = F: [Ph 3 C] [250] R = HX= F: H [250] ;R= Et X = F: H [250] R = HX= F: Bu [98] Angewandte Chemie Reviews [93] ;L i(C 7 H 8 ) [515] ;N a(C 6 H 6 ) 2 [515] ;K -(C 6 H 6 ) 2 [515] ;Rb(C 6 H 6 ) 2 [515] ;C s [93] Cs-(C 6 H 6 ) 2 [515] ;Tl(C 6 H 6 ) 2 [515] Ag [93] [HCB 11 X 6 Me 5 ] À (X = Cl:, Br,o rI ) Cs [94] ;H [94] ;C 6 H 6 [94] C 6 H 6 [264] ;1,3,5-(Me) 3 C 6 H 3 [264] ; Et 2 O [516] ;thf [516] [CB 11 X 6 H 6 ] À X = I: Cs [97] ; X = Br:Cs [95] ;Tl(C 7 H 8 ) 2 [517] X = I: Ag [97] ; X = Cl:Ag [97] ; X = Br:A g [518] X = I: [Ph 3 C] [97] ; X = Cl:…”

Section: Resultsmentioning

confidence: 99%

Taming the Cationic Beast: Novel Developments in the Synthesis and Application of Weakly Coordinating Anions

et al. 2018

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This Review gives a comprehensive overview of the most topical weakly coordinating anions (WCAs) and contains information on WCA design, stability, and applications. As an update to the 2004 review, developments in common classes of WCA are included. Methods for the incorporation of WCAs into a given system are discussed and advice given on how to best choose a method for the introduction of a particular WCA. A series of starting materials for a large number of WCA precursors and references are tabulated as a useful resource when looking for procedures to prepare WCAs. Furthermore, a collection of scales that allow the performance of a WCA, or its underlying Lewis acid, to be judged is collated with some advice on how to use them. The examples chosen to illustrate WCA developments are taken from a broad selection of topics where WCAs play a role. In addition a section focusing on transition metal and catalysis applications as well as supporting electrolytes is also included.

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“…In pursuit of our efforts to establish reproducible procedures 30 for the synthesis of [HCB 11 Cl 11 ]from the parent [HCB 11 H 11 ]anion, 13 we at one point examined treatment of Cs[HCB 11 H 11 ] with Cl 2 gas in refluxing triflic acid. In at least one experiment, we observed production of Cs[HCB 11 Cl 9 (OTf) 2 ] as the dominant product with the triflyloxy (triflato) substituents apparently in the 35 7,12-positions as evidenced from an XRD study on a single crystal (Fig.…”

mentioning

confidence: 99%

“…The outcomes of these reactions 20 are analogous to those with a halogen in place of OTf. 1,13 Cesium salts of the tris-triflyloxy and mono-triflyloxy halogen substituted anions were isolated after workup with Cs 2 CO 3 followed by recrystallization. The 19 32 The modest pyramidalization about the Si centers (sums of C-Si-C angles of 344-346°) 30 is similar to the various weak R 3 Si + adducts.…”

mentioning

confidence: 99%