Bis(2,4,6-triisopropylphenyl)tin(IV) compounds: Synthesis, single-crystal X-ray characterization and reactivity toward ionizing species and polar monomers

Annunziata, Liana; Pappalardo, Daniela; Tedesco, Consiglia; Antinucci, Simona; Pellecchia, Claudio

doi:10.1016/j.jorganchem.2005.12.011

Cited by 6 publications

(12 citation statements)

References 27 publications

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“…Bis(2,4,6-tri-iso-propoxyphenyl)tin(IV) derivatives (371-373, Chart 54) were screened for 3-caprolactone polymerisation. 170,171 They were active polymerisation catalysts and complex 373 displayed poor activity, affording 86% conversion after 24 h at 75 C and for a monomer : metal ratio of 120 : 1.…”

Section: Other Ligand Systemsmentioning

confidence: 99%

Metal catalysts for ε-caprolactone polymerisation

2010

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Economic pressure, environmental issues and ever increasing demand are driving the shift from oil-based polymers to those available from renewable resources. Ring opening polymerisation of cyclic esters is currently a topical field with metal complex-induced coordination/insertion type polymerisation leading the way. Such a polymerisation method offers a wide range of advantages from control over the polymer structure to kinetic enhancement; however industrially available catalysts based on tin suffer from inherent toxicity and as a result a policy change from the Food and Drug Administration (FDA) is not unrealistic. This review underlines the efforts made in the past five years or so, and shows how low toxicity metals are attracting increasing attention in the field of e-caprolactone polymerisation

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Section: Other Ligand Systemsmentioning

confidence: 99%

Metal catalysts for ε-caprolactone polymerisation

2010

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“…A π interaction of the benzyl group to the tin centre was previously recognized by NMR for the cationic species Tip 2 SnBz + (Tip = 2,4,6‐triisopropylphenyl) 21…”

Section: Resultsmentioning

confidence: 79%

Octahedral Alkylbis(phenoxy‐imine)tin(IV) Complexes: Effect of Substituents on the Geometry of the Complexes and Their Reactivity Toward Ionizing Species and Ethylene

et al. 2007

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The synthesis and characterization of the organo-tin compounds L 2 SnR 2 [L = N-(3,5-dichlorosalicylidene)aniline; R = CH 3 (1), R = CH 2 Ph (2)] and LЈ 2 SnR 2 [3: LЈ = N-(3-tert-butylsalicylidene)aniline, R = CH 2 Ph] are described herein. NMR studies showed a highly symmetric structure for complex 1, with the alkyl groups in a trans configuration, and the presence of at least two isomers in fluxional equilibrium for compounds 2 and 3. Single-crystal X-ray characterization for compound 2 showed an octahedral geometry with the alkyl groups in trans relationship. The reactivity of the synthesized compounds toward ionizing agents was studied by NMR spectroscopy. For compounds 1 and 2 formation of cationic

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“…ε-Caprolactone was distilled in vacuum from CaH 2 prior to use. The benzylbromobis(2,4,6-triisopropylphenyl)tin was synthesized according to a previously reported procedure . NMR spectra were recorded on Bruker Avance 400 (Avance 1) and 500 (Avance 2) MHz spectrometers ( 1 H, 400.00 MHz; 13 C, 100.57 MHz; 119 Sn, 149.09 MHz and 1 H, 500.13 MHz; 13 C, 125.77 MHz; 119 Sn, 186.49 MHz, respectively).…”

Section: Methodsmentioning

confidence: 99%

“…16 We recently reported the synthesis of tin(IV) compounds of general formula Tip 2 SnR 2 (Tip ) 2,4,6-triisopropylbenzene; R ) alkyl, halogen) and studied their reactivity toward ionizing agents and toward 1,4-butadiene, propylene oxide, and -caprolactone. 17 The obtained cationic species were able to act as initiator in the ROP of -caprolactone. In order to establish whether a "coordination-insertion" mechanism could be active in this kind of system, we substituted an alkyl group for an alkoxy group and studied the reactivity of the compounds in the -caprolactone ring-opening polymerization.…”

Section: Introductionmentioning

confidence: 98%

“…We recently reported the synthesis of tin(IV) compounds of general formula Tip 2 SnR 2 (Tip = 2,4,6-triisopropylbenzene; R = alkyl, halogen) and studied their reactivity toward ionizing agents and toward 1,4-butadiene, propylene oxide, and ε-caprolactone . The obtained cationic species were able to act as initiator in the ROP of ε-caprolactone.…”

Section: Introductionmentioning

confidence: 99%

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Ring-Opening Polymerization of ε-Caprolactone by Benzylalkoxybis(2,4,6-triisopropylphenyl)tin Compounds: Observation of the Insertion Product into the Sn−OMe Bond

et al. 2007

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Benzylmethoxybis(2,4,tin (1) and benzylisopropoxybis(2,4,6-triisopropylphenyl)tin (2) were synthesized and characterized. Compound 1 exhibited good activity in the ring-opening polymerization of -caprolactone, in a liVing fashion, under mild conditions. The polymerization was demonstrated to proceed via ring-opening of the monomer at the acyl-oxygen bond. The -caprolactone insertion product into the Sn-OCH 3 of the initiator was characterized, providing support for a "coordination-insertion" mechanism.

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Bis(2,4,6-triisopropylphenyl)tin(IV) compounds: Synthesis, single-crystal X-ray characterization and reactivity toward ionizing species and polar monomers

Cited by 6 publications

References 27 publications

Metal catalysts for ε-caprolactone polymerisation

Metal catalysts for ε-caprolactone polymerisation

Octahedral Alkylbis(phenoxy‐imine)tin(IV) Complexes: Effect of Substituents on the Geometry of the Complexes and Their Reactivity Toward Ionizing Species and Ethylene

Ring-Opening Polymerization of ε-Caprolactone by Benzylalkoxybis(2,4,6-triisopropylphenyl)tin Compounds: Observation of the Insertion Product into the Sn−OMe Bond

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