Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: an efficient synthesis of dithiocarboxylic esters

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

doi:10.1016/s0040-4039(01)00570-6

Cited by 104 publications

(36 citation statements)

References 16 publications

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“…All other CTAs were prepared using a procedure developed in our laboratory. [30,31] The purity of all CTAs was confirmed by means of 1 H NMR, 13 C NMR and IR spectroscopy, as well as GC-MS and found to be A99%. All other reagents used for solution and emulsion polymerizations were of high purity.…”

Section: Experimental Partmentioning

confidence: 96%

Reversible Addition-Fragmentation Chain-Transfer Polymerization for the Synthesis of Poly(4-acetoxystyrene) and Poly(4-acetoxystyrene)-block-polystyrene by Bulk, Solution and Emulsion Techniques

Kanagasabapathy

Sudalai

Benicewicz

2001

Macromol. Rapid Commun.

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Section: Experimental Partmentioning

confidence: 96%

Reversible Addition-Fragmentation Chain-Transfer Polymerization for the Synthesis of Poly(4-acetoxystyrene) and Poly(4-acetoxystyrene)-block-polystyrene by Bulk, Solution and Emulsion Techniques

Kanagasabapathy

Sudalai

Benicewicz

2001

Macromol. Rapid Commun.

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“…[44,116,117] This procedure has been used to prepare cumyl dithiobenzoate (Scheme 10). [9,14] unfortunately give Michael-like addition (sulfur at unsubstituted position).…”

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

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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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“…12 Among of them, it can catalyze the addition of thio-compounds to alkenes. 13 The reaction of (R)-limonene with S-thioacetic acid (1 mol equiv.) in the presence of catalytic K-10 clay (10% weight of limonene) in refluxing toluene for 3.5 h led to 9-[(4R)-p-menthenyl] S-thioacetate as a 1:1 mixture of diastereoisomers in 65% yield, along with unreacted limonene (10%) and several minor products, such as isomeric p-menthadienes (among of them terpinolene (2)) and p-cymene (3) -Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

“…This can be explained in terms of a concerted S-H addition to the acyclic double bond of the substrate with steric factors controlling the regioselectivity. 13 Another possible explanation could be the attack of the acyclic double bond of limonene onto the protonated S-thioacid to afford a tertiary carbenium ion iv.…”

Section: Resultsmentioning

confidence: 99%

The reaction of (R)-limonene with S-thioacids

Mattos¹,

Bernini²

2007

J. Braz. Chem. Soc.

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A reação do (R)-limoneno com uma quantidade equimolar de ácidos S-tioacético ou Stiobenzóico em tolueno sob refluxo ocorre com regiosseletividade anti-Markovnikoff produzindo os 9-[(4R, 8RS)-p-mentenil] S-tiocarboxilatos em 71 e 61% de rendimento, respectivamente. A mesma reação do ácido S-tioacético catalisada pela argila montmorilonita K-10 levou ao Stioéster em 65% de rendimento, além de p-mentadienos e p-cimeno. Foi observado que a argila K-10 promove a isomerização do limoneno aos mentadienos, e sua disproporcionação para o pcimeno The reaction of (R)-limonene with equimolar amount of S-thioacetic or S-thiobenzoic acids in refluxing toluene proceeded regioselectively in anti-Markovnikoff fashion forming 9-[(4R, 8RS)-p-menthenyl] S-thiocarboxylates (71 and 61% yield, respectively). The montmorillonite K-10 clay-catalyzed reaction of (R)-limonene with S-thioacetic acid led to the S-thioester (65%) along with p-menthadienes and p-cymene. It was observed that K-10 clay promoted the isomerization of limonene to p-menthadienes and further disproportionation to p-cymene.

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Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: an efficient synthesis of dithiocarboxylic esters

Cited by 104 publications

References 16 publications

Reversible Addition-Fragmentation Chain-Transfer Polymerization for the Synthesis of Poly(4-acetoxystyrene) and Poly(4-acetoxystyrene)-block-polystyrene by Bulk, Solution and Emulsion Techniques

Reversible Addition-Fragmentation Chain-Transfer Polymerization for the Synthesis of Poly(4-acetoxystyrene) and Poly(4-acetoxystyrene)-block-polystyrene by Bulk, Solution and Emulsion Techniques

Living Radical Polymerization by the RAFT Process

The reaction of (R)-limonene with S-thioacids

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