Phosphorus Pentasulfide:  A Mild and Versatile Catalyst/Reagent for the Preparation of Dithiocarboxylic Esters

Sudalai, Arumugam; Kanagasabapathy, Subbareddy; Benicewicz, Brian C.

doi:10.1021/ol006407q

Cited by 77 publications

(46 citation statements)

References 15 publications

(9 reference statements)

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“…It is also possible to use this chemistry to generate a RAFT agent in situ during polymerization. [45] • Sulfuration of a thioloester, [14,44] a carboxylic acid plus an alcohol [120] or a carboxylic acid with a halide or olefin [121] with P 4 S 10 , or Davey or Lawesson's reagent (Scheme 12).…”

Section: Synthesis Of Raft Agentsmentioning

confidence: 99%

See 1 more Smart Citation

Living Radical Polymerization by the RAFT Process

Moad¹,

Rizzardo²,

Thang³

2005

Aust. J. Chem.

2,147

1,894

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This paper presents a review of living radical polymerization achieved with thiocarbonylthio compounds [ZC( S)SR] by a mechanism of reversible addition-fragmentation chain transfer (RAFT). Since we first introduced the technique in 1998, the number of papers and patents on the RAFT process has increased exponentially as the technique has proved to be one of the most versatile for the provision of polymers of well defined architecture. The factors influencing the effectiveness of RAFT agents and outcome of RAFT polymerization are detailed. With this insight, guidelines are presented on how to conduct RAFT and choose RAFT agents to achieve particular structures. A survey is provided of the current scope and applications of the RAFT process in the synthesis of well defined homo-, gradient, diblock, triblock, and star polymers, as well as more complex architectures including microgels and polymer brushes.

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Section: Synthesis Of Raft Agentsmentioning

confidence: 99%

“…These include the reaction of benzyl chloride [9,123] or a benzyl sulfone [124] with elemental sulfur in the presence of base, reaction of phenyl Grignard reagent with carbon disulfide, [9] and treatment of benzoic acid with P 4 S 10 or Davey reagent. [121,125] …”

Section: Synthesis Of Raft Agentsmentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process

Moad¹,

Rizzardo²,

Thang³

2005

Aust. J. Chem.

2,147

1,894

View full text Add to dashboard Cite

show abstract

“…[35,36] In the second method, carboxyl moieties are converted to acyl chloride groups in the presence of thionyl chloride after which the acyl chlorides are reacted with a magnesium chloride dithiopropanoate salt to produce bis-dithioesters. [33,34] Of the available methods for chemical functionalization of CNTs, fluorination is emerging as an important process for nanotube modification.…”

Section: Cnt Preparationmentioning

confidence: 99%

Carbon Nanotubes Anchored to Silicon for Device Fabrication

et al. 2010

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This report highlights recent progress in the fabrication of vertically aligned carbon nanotubes (VA-CNTs) on silicon-based materials. Research into these nanostructured composite materials is spurred by the importance of silicon as a basis for most current devices and the disruptive properties of CNTs. Various CNT attachments methods of covalent and adsorptive nature are critically compared. Selected examples of device applications where the VA-CNT on silicon assemblies are showing particular promise are discussed. These applications include field emitters, filtration membranes, dry adhesives, sensors and scaffolds for biointerfaces.

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“…Benzyl thiophene-2-carbodithioate (BTCT) and 2-methyl-2-(4-methylcyclohex-3-enyl)propyl thiophene-2-carbodithioate (MCPT) were synthesized through the coupling of thiophene-2-carboxylic acid with phenyl methanol and 2-methyl-2-(4-methylcyclohex-3-enyl)propan-1-ol under P 4 S 10 according to the literature, [36][37][38] respectively. A typical preparation procedure for BTCT can be described as follows: Thiophene-2-carboxylic acid (1.29 g, 10 mmol), phenyl methanol (1.09 g, 10 mmol), P 4 S 10 (2.22 g, 5 mmol), and 40 mL of benzene were added to a 100-mL, three-necked round flask.…”

Section: Synthesis Of the Raft Agentsmentioning

confidence: 99%

Reversible addition–fragmentation chain transfer polymerization of styrene using a novel thiophene dithioester as the reversible addition–fragmentation chain transfer agent

Zhou

Zhu

et al. 2007

J of Applied Polymer Sci

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Benzyl thiophene-2-carbodithioate and 2-methyl-2-(4-methylcyclohex-3-enyl)propyl thiophene-2-carbodithioate were synthesized. The reversible addition-fragmentation chain transfer polymerizations of styrene with benzyl thiophene-2-carbodithioate and 2-methyl-2-(4-methylcyclohex-3-enyl)propyl thiophene-2-carbodithioate as chaintransfer agents and with 2,2 0 -azobisisobutyronitrile as an initiator were carried out. The polymerization kinetics were investigated. An ab initio calculation method was used to explore the differences between benzyl thiophene-2-carbodithioate and benzyl benzodithioate. The structure of the obtained polymers was characterized with 1 H-NMR. Chain-extension experiments of the obtained polymer with styrene were carried out.

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Phosphorus Pentasulfide: A Mild and Versatile Catalyst/Reagent for the Preparation of Dithiocarboxylic Esters

Abstract: The reaction of carboxylic acids (1) with a variety of thiols or alcohols in the presence of phosphorus pentasulfide (P(4)S(10)) as a catalyst and reagent (20-40 mol %) proceeded effectively to afford the corresponding dithiocarboxylic esters (2) in high yields.

Cited by 77 publications

References 15 publications

Living Radical Polymerization by the RAFT Process

Living Radical Polymerization by the RAFT Process

Carbon Nanotubes Anchored to Silicon for Device Fabrication

Reversible addition–fragmentation chain transfer polymerization of styrene using a novel thiophene dithioester as the reversible addition–fragmentation chain transfer agent

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