One Pot Phase Transfer Synthesis of Trithiocarbonates from Carbon Bisulphide and Alkyl Halides

Lee, Albert W. M.; Chan, Wing Hong; Wong, H. C.

doi:10.1080/00397918808081310

Cited by 77 publications

(20 citation statements)

References 7 publications

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“…Two efficient approaches have been reported for the preparation of trithiocarbonate. One involves dialkylation of the trithiocarbonate anion with alkyl halides in a two‐phase system using an onium salt as a phase‐transfer agent17, 30 (Scheme ). Tamami and Kiasat31 have reported a new approach of easy and efficient one‐step synthesis of symmetrical dialkyl trithiocarbonates directly from carbon disulfide and alkyl halides using a commercially available hydroxide form of an anion exchange resin (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Controlled free radical photopolymerization of styrene initiated by trithiocarbonate

Ran

Wan

Gao

et al. 2007

Polymer International

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Density functional theory calculations are reported for prediction of the trends in CS bond dissociation energies and atomic spin densities for radicals using S,S′‐bis(α,α′‐dimethyl‐α‐acetic acid) trithiocarbonate (TTCA) and bis(2‐oxo‐2‐phenylethyl) trithiocarbonate (TTCB) as reversible addition fragmentation chain transfer (RAFT) reagents. The calculations predict that the value of the CS bond length (1.865 Å) of TTCA is longer than that (1.826 Å) of TTCB, and TTCA is more effective for the polymerization of styrene (St) compared to TTCB as predicted by density functional theory. In photopolymerizations, pseudo‐first‐order kinetics were confirmed for TTCB‐mediated photopolymerization of St due to the linear increase of ln([M]0/[M]) up to about 28% conversion, suggesting the living characteristics behavior of the photopolymerization of St in the presence of TTCB. For both TTCA and TTCB the polydispersities change with increasing conversion in the range 1.10–1.45, typical for RAFT‐prepared (co)polymers and well below the theoretical lower limit of 1.50 for a normal free radical polymerization. In addition, the triblock copolymer polystyrene‐block‐poly(butyl acrylate)‐block‐polystyrene (PSPBAPS) was successfully prepared, with very good control over molecular weight and narrow polydispersity (Mw/Mn = 1.45), using PSSC(S)SPS as macro‐photoinitiator under UV irradiation at room temperature. This indicated that this reversible and valid strategy led to a better controlled block copolymer with defined structures. Copyright © 2007 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Controlled free radical photopolymerization of styrene initiated by trithiocarbonate

Ran

Wan

Gao

et al. 2007

Polymer International

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“…BP was recrystallized twice from ethanol and used as photo-initiator. DBTTC was synthesized according to the literature [21].…”

Section: Methodsmentioning

confidence: 99%

Thermo- and pH-responsive polypropylene microporous membrane prepared by the photoinduced RAFT-mediated graft copolymerization

Zhou

et al. 2009

Journal of Membrane Science

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“…The precursor Fe 3 (CO) 12 was prepared using the literature procedure. 25 1,3-dithiolane-2thione, 26 1,3-dithiolan-2-one (L 1 ), 27 1,4-dithian-2-one (L 2 ) 28 and 1,4-dithiepan-5-one (L 3 ) 29 were synthesized following literature methods with slight modifications. 1,2-ethaneditiol was purchased from Alfa Aesar.…”

Section: General Proceduresmentioning

confidence: 99%

“…As shown in Scheme 1, cyclic thioester ligands L 1−3 with the same fragment, "SCH 2 CH 2 SCO", were prepared by following the literature procedures via two-step (L 1 ) or one-step (L 2−3 ) reactions. [27][28][29] Heating a solution of L 1−3 and Fe 3 (CO) 12 (1/1) in tetrahydrofuran under reflux resulted in the formation of complex 1, [Fe 2 (μ-S 2 C 2 H 4 )(CO) 6 ], a widely reported diiron complex 23,24 (Scheme 2). For ligand L 1 , this complex was the solely isolable product.…”

Section: Synthesismentioning

confidence: 99%

Reaction of three cyclic thioester ligands with triiron dodecacarbonyl and possible reaction mechanisms

et al. 2017

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Three cyclic thioesters of the formula "−SCH 2 CH 2 SCO(CH 2) n −" (L 1 , n = 0; L 2 , = 1, L 3 , n = 2) and their reactions with Fe 3 (CO) 12 are reported. All the reactions produced a known diiron complex, [Fe 2 (μ-S 2 C 2 H 4)(CO) 6 ] (1), which suggested that in the reactions, cleavage of C-S bond to generate "SCH 2 CH 2 S" fragment is a common pathway for all the three ligands. In the case of ligand L 2 , a new complex 2, [Fe 2 {μ-SC 2 H 4 (SCH 2)-κ}(CO) 6 ] was isolated and structurally characterized. In the reaction of ligand L 3 , an unknown iron carbonyl product was isolated in addition to complex 1. Although its precise structure was not established due to its instability and low yield, its infrared spectrum and decomposing into complex 1 implied that the product may be a cluster with higher nuclearity. The experimental observations suggested that with the increase of the ring size of the cyclic thioester ligands, further bond cleavages were involved in the reaction in addition to that leading to complex 1.

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One Pot Phase Transfer Synthesis of Trithiocarbonates from Carbon Bisulphide and Alkyl Halides

Cited by 77 publications

References 7 publications

Controlled free radical photopolymerization of styrene initiated by trithiocarbonate

Controlled free radical photopolymerization of styrene initiated by trithiocarbonate

Thermo- and pH-responsive polypropylene microporous membrane prepared by the photoinduced RAFT-mediated graft copolymerization

Reaction of three cyclic thioester ligands with triiron dodecacarbonyl and possible reaction mechanisms

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