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Journal ArticleDOI

Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification

01 Aug 1991-Journal of Organic Chemistry (American Chemical Society)-Vol. 56, Iss: 18, pp 5307-5311
About: This article is published in Journal of Organic Chemistry.The article was published on 1991-08-01. It has received 323 citations till now. The article focuses on the topics: Transesterification & Catalysis.
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Patent
24 Mar 2000
TL;DR: In this paper, the degradation times of polyhydroxyalkanoates are controlled under physiological conditions, and the degradation rates are controlled with less than one year under certain physiological conditions.
Abstract: Devices formed of or including biocompatible polyhydroxyalkanoates are provided with controlled degradation rates, preferably less than one year under physiological conditions. Preferred devices include sutures, suture fasteners, meniscus repair devices, rivets, tacks, staples, screws (including interference screws), bone plates and bone plating systems, surgical mesh, repair patches, slings, cardiovascular patches, orthopedic pins (including bone filling augmentation material), adhesion barriers, stents, guided tissue repair/regeneration devices, articular cartilage repair devices, nerve guides, tendon repair devices, atrial septal defect repair devices, pericardial patches, bulking and filling agents, vein valves, bone marrow scaffolds, meniscus regeneration devices, ligament and tendon grafts, ocular cell implants, spinal fusion cages, skin substitutes, dural substitutes, bone graft substitutes, bone dowels, wound dressings, and hemostats. The polyhydroxyalkanoates can contain additives, be formed of mixtures of monomers or include pendant groups or modifications in their backbones, or can be chemically modified, all to alter the degradation rates. The polyhydroxyalkanoate compositions also provide favorable mechanical properties, biocompatibility, and degradation times within desirable time frames under physiological conditions.

1,000 citations

Patent
22 Dec 1998
TL;DR: In this article, a wide range of biocompatible poly(4HB) compositions with controlled degradation rates have been developed, including foams, coatings, meshes, and microparticles.
Abstract: Biocompatible polyhydroxyalkanoate compositions with controlled degradation rates have been developed. In one embodiment, the polyhydroxyalkanoates contain additives to alter the degradation rates. In another embodiment, the polyhydroxyalkanoates are formed of mixtures of monomers or include pendant groups or modifications in their backbones to alter their degradation rates. In still another embodiment, the polyhydroxyalkanoates are chemically modified. Methods for manufacturing the devices which increase porosity or exposed surface area can be used to alter degradability. For example, as demonstrated by the examples, porous polyhydroxyalkanoates can be made using methods that creates pores, voids, or interstitial spacing, such as an emulsion or spray drying technique, or which incorporate leachable or lyophilizable particles within the polymer. Examples describe poly(4HB) compositions including foams, coatings, meshes, and microparticles. As demonstrated by the examples, these polyhydroxyalkanoate compositions have extremely favorable mechanical properties, as well as are biocompatible and degrade within desirable time frames under physioogical conditions. These polyhydroxyalkanoate materials provide a wider range of polyhydroxyalkanoate degradation rates than are currently available. Methods for processing these materials, particularly for therapeutic, prophylactic or diagnostic applications, or into devices which can be implanted or injected, are also described.

763 citations

Journal ArticleDOI
TL;DR: In this article, the authors used 2-methyl-6-nitrobenzoic anhydride with triethylamine as a basic catalyst for the condensation reaction.
Abstract: Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety of lactones are also prepared in high yields at room temperature from the corresponding ω-hydroxycarboxylic acids with use of 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods are successfully applied to the synthesis of erythro-aleuritic acid lactone and an eight-membered-ring lactone moiety of octalactins A and B. The efficiency of the cyclizations is compared to those of other reported lactonizations.

342 citations

Journal ArticleDOI
TL;DR: On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained and chemospecific, three-component reactions under DBSA-catalyzed conditions were found to proceed smoothly.
Abstract: Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

338 citations

Journal ArticleDOI
10 Nov 2000-Science
TL;DR: It is shown that the direct condensation of equimolar amounts of carboxylic acids and alcohols can be achieved with the use of hafnium(IV) salts, such as commercially available ha fnium( IV) chloride and hafnia(IV), which may be suitable for large-scale operations.
Abstract: In order to promote atom efficiency in synthesis and to avoid the generation of environmental waste, the use of stoichiometric amounts of condensing reagents or excess substrates should be avoided. In esterification, excesses of either carboxylic acids or alcohols are normally needed. We show that the direct condensation of equimolar amounts of carboxylic acids and alcohols can be achieved with the use of hafnium(IV) salts, such as commercially available hafnium(IV) chloride and hafnium(IV) tert-butoxide. The present method can be applied to direct polyesterification and may be suitable for large-scale operations.

298 citations