Solventless Reactions for the Synthesis of Organotin Clusters and Cages

Chandrasekhar, Vadapalli; Baskar, Viswanathan; Boomishankar, Ramamoorthy; Gopal, Kandasamy; Zacchini, Stefano; Bickley, Jamie F.; Steiner, Alexander

doi:10.1021/om030338c

Cited by 61 publications

(41 citation statements)

References 37 publications

(24 reference statements)

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“…[4a,b] Alternatively, a novel solvent-free methodology, which we have recently demonstrated, can also be adopted. [10] In this latter technique the reactants are ground together for a specified period of time. This was followed by a workup to afford the final products (see Experimental Section).…”

Section: Resultsmentioning

confidence: 99%

“…[9,10] The tin atom is involved in four covalent bonds to three phenyl groups and one carboxylate oxygen atom. The other carboxylate oxygen atom undergoes a fifth weaker bonding interaction to the tin atom along the tetrahedral face.…”

Section: Resultsmentioning

confidence: 99%

“…At the completion of the grinding period the product was extracted with CH 2 Cl 2 and crystallized. [10] The stoichiometric ratio of the reactants, the yields, and the characterization data of the products 1-7 are given below. X-ray crystal structure determination of 1-4 and 6: Single crystals of 1 were obtained from the reaction mixture at room temperature.…”

Section: Methodsmentioning

confidence: 99%

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Organostannoxane‐Supported Multiferrocenyl Assemblies: Synthesis, Novel Supramolecular Structures, and Electrochemistry

Chandrasekhar

Gopal

Nagendran

et al. 2005

Chemistry A European J

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Organostannoxane-based multiredox assemblies containing ferrocenyl peripheries have been readily synthesized by a simple one-pot synthesis, either by a solution method or by room-temperature solid-state synthesis, in nearly quantitative yields. The number of ferrocenyl units in the multiredox assembly is readily varied by stoichiometric control as well as by the choice of the organotin precursors. Thus, the reaction of the diorganotin oxides, R2SnO (R = Ph, nBu and tBu) with ferrocene carboxylic acid affords tetra-, di-, and mononuclear derivatives [{Ph2Sn[OC(O)Fc]2}2] (1), [{[nBu2SnOC(O)Fc]2O}2] (2), [nBu2Sn{OC(O)Fc}2] (3), [{tBu2Sn(OH)OC(O)Fc}2] (4), and [tBu2Sn{OC(O)Fc}2] (5) (Fc = eta(5)C5H4-Fe-eta(5)C5H5). The reaction of triorganotin oxides, R3SnOSnR3 (R = nBu and Ph) with ferrocene carboxylic acid leads to the formation of the mono-nuclear derivatives [Ph3SnOC(O)Fc] (6) and [{nBu3SnOC(O)Fc}(n)] (7). Molecular structures of the compounds 1-4 and 6 have been determined by single-crystal X-ray analysis. The molecular structure of compound 1 is new among organotin carboxylates. In this compound, ferrocenyl carboxylates are involved in both chelating and bridging coordination modes to the tin atoms to form an eight-membered cyclic structure. In all of these compounds, the acidic protons of the cyclopentadienyl groups are hydrogen bonded to the carboxylate oxygens (C-HO) to form rich supramolecular assemblies. In addition to this, pi-pi, T-shaped, L-shaped, and side-to-face stacking interactions involving ferrocenyl groups also occur. Compound 6 shows an interesting and novel intermolecular CO2-pi stacking interaction. Electrochemical analysis of the compounds 1-4, 6, and 7 shows a single, quasi-reversible oxidation peak corresponding to the simultaneous oxidation of four, two, and one ferrocenyl substituents, respectively. Compound 5 shows two quasi-reversible oxidation peaks. This is attributed to the positional difference among the ferrocenyl substituents on the tin atom. Additionally, while compounds 2 and 4 are electrochemically quite robust and do not decompose even after ten continuous CV cycles, compounds 1, and 3, 5-7 start to show decomposition after five cycles.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Organostannoxane‐Supported Multiferrocenyl Assemblies: Synthesis, Novel Supramolecular Structures, and Electrochemistry

Chandrasekhar

Gopal

Nagendran

et al. 2005

Chemistry A European J

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“…This produced in excellent yields a variety of organotin clusters and cages with complicated but well-defined architectures (Scheme 28). [275] Scheme 28 A mechanochemical organotin reaction.…”

Section: Main-group Compoundsmentioning

confidence: 99%

Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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Citation for published item:tmesD F vF nd edmsD gF tF nd folmD gF nd frgD hF nd gollierD F nd pri § s § i¡ D F nd qrepioniD pF nd rrrisD uF hF wF nd ryettD qF nd tonesD F nd uresD eF nd wkD tF nd winiD vF nd yrpenD eF qF nd rkinD sF F nd herouseD F gF nd teedD tF F nd ddellD hF gF @PHIPA 9wehnohemistry X opportunities for new nd lener synthesisF9D ghemil soiety reviewsFD RI @IAF ppF RIQERRUF Further information on publisher's website: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

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“…Considering the industrial and biological utilization of organotin carboxylates, a much faster and environmentally benign method for their synthesis is desired. Chandrasekhar et al have recently reported the synthesis of organotin carboxylates having most commonly observed structure using a solventless methodology where the starting materials are ground together [11]. The only limitations of this very useful method are the relatively slower rates and the hazards associated with prolonged grinding of the reaction mixture (organotin carboxylates are known to have anti-neoplastic properties) [12].…”

Section: Introductionmentioning

confidence: 99%