Staudinger’s phosphazene as an efficient esterifying reagent

Dinesh, Murugan; Raja, R.; Archana, Sivasubramaniyan; Sathishkumar, Murugan; Banu, Mohamed Sulthan Roshan; Ponnuswamy, Alagusundaram

doi:10.1080/00397911.2016.1211705

Cited by 3 publications

(1 citation statement)

References 16 publications

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“…For examples, polymerbounded Ph 3 P (or Ph 3 P)/I 2 /microwave [20][21][22][23] and Ph 3 P/I 2 /Zn(OTf) 2 condition [24] have been reported, because the combination of PPh 3 and I 2 in the presence of the base has been well known so far [25,26]. In addition, the use of Ph 2 PCl/I 2 /imidazole [27], Ph 3 PBr 2 [28], POCl 3 / DMAP/Et 3 N [29], or PPh 3 /BnN 3 /microwave (Staudinger's phosphazene) [30] systems was found to be effective for the esterification. The hypervalent iodine reagents could be utilized in coupling reactions [31,32].…”

Section: Synthesis Of Carboxylic Acid Esters Using Carboxylic Acids Amentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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In this chapter, recent advances in the synthesis of carboxylic acid esters are summarized based on the utilization of carboxylic acids as electrophiles or nucleophiles in reactions. Condensation reagents or catalysts connect the carboxylic acids with the alcohols to afford the corresponding esters, together with the formation of 1 equiv. of H 2 O, in which the carboxylic acids can be regarded as the electrophile. In contrast, the carboxylate ion intermediates derived from the carboxylic acids react with alkyl halides, carbocations, or their equivalents to produce the esters, in which the carboxylate ions from the carboxylic acids can be regarded as the nucleophile. This chapter mainly introduces the recent progress in this field of the formation of esters, based on the classification of the role of carboxylic acids in reactions.

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Section: Synthesis Of Carboxylic Acid Esters Using Carboxylic Acids Amentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Yıldırım

Mudaber

Öztürk

2018

Euro J Lipid Sci & Tech

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Biological wax esters are important commercial products used in various industrial and medicinal fields. These valuable compounds can be synthesized via several chemical and enzymatic reactions which have some advantages and more disadvantages. In particular, many strong acid catalysts cause undesirable structural changes in unsaturated fatty acids molecules. In the present study, easily accessible 1‐hexadecyl‐3‐sulfoimidazolium chloride as an ionic liquid is screened as a mild Brønsted acid metal free catalyst for the chemical esterification, or transesterification, of equimolar amounts of long chain fatty acids or fatty acid methyl esters, respectively, with fatty alcohols in a solventless medium. The various parameters affecting the yield of the wax ester are optimized, catalyst reuse studies, and large scale synthesis are also carried out. According to this alternative practical and green process, a series of wax esters (17 examples) are produced readily in good to excellent yields. There is no undesirable geometric cis‐trans isomerization in unsaturated fatty acids under the reaction conditions used. The catalyst is also quite effective when triglycerides are converted directly to the wax esters via transesterification reaction. Practical Applications: With an effortless and environmentally friendly method developed in this study, various wax esters can be synthesized as valuable industrial materials. In order to synthesis these esters, there is not any restriction for starting compounds. The most important aspect of the developed procedures is that metallic or strong aggressive acidic catalysts are not used compared to existing procedures. It is possible to carry out large‐scale syntheses of esters with high yields. In the present study, a series of industrial and medical important wax esters are synthesized from renewable sources in a solvent‐free environment using IL‐catalyzed environmentally friendly methods.

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Phosphazene Bases as Organocatalysts for Ring‐Opening Polymerization of Cyclic Esters

Liu

Ren

Zhao

et al. 2018

Macromol. Rapid Commun.

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Over the past several years, organocatalyzed polymerization reactions have attracted considerable attention, and these efforts have led to major advances. A large number of organic compounds have been proven active for the polymerization of a large variety of monomers. In particular, phosphazene bases (PBs) are a family of extremely strong, non‐nucleophilic, and uncharged auxiliary bases, and have shown their remarkable potential as organocatalysts for the ring‐opening polymerization (ROP) of cyclic monomers. By deprotonation of weak acids or in combination with lithium cation, PBs significantly enhance the nucleophilicity of the initiator/chain‐end, thus allowing fast and usually controlled anionic polymerization. In this feature article, the recent advances in phosphazene‐catalyzed ROP of cyclic esters are summarized. This review is divided into three sections, including general features, design and synthesis, and catalytic applications. It aims to provide a critical analysis of PB‐mediated ROP systems and a useful guide for the further design of organocatalysts applied to polymer synthesis. An outlook is given at the end.

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Staudinger’s phosphazene as an efficient esterifying reagent

Cited by 3 publications

References 16 publications

Recent Advances in the Synthesis of Carboxylic Acid Esters

Recent Advances in the Synthesis of Carboxylic Acid Esters

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Phosphazene Bases as Organocatalysts for Ring‐Opening Polymerization of Cyclic Esters

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