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Journal ArticleDOI

Microwave Induced Ferrier Rearrangement

01 Aug 1994-Synthetic Communications (Taylor & Francis Group)-Vol. 24, Iss: 15, pp 2097-2101

AbstractA short and facile entry to the 2, 3-unsaturated O-arylglyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.

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Citations
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2,405 citations

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1,305 citations

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TL;DR: The purpose of this critical review is to highlight the advances in this general area by presenting such newer applications in organic synthesis by presenting microwave, ultrasound, sunlight, mechanochemical mixing and other alternative means of activation.
Abstract: Microwave, ultrasound, sunlight and mechanochemical mixing can be used to augment conventional laboratory techniques. By applying these alternative means of activation, a number of chemical transformations have been achieved thereby improving many existing protocols with superior results when compared to reactions performed under traditional conditions. The purpose of this critical review is to highlight the advances in this general area by presenting such newer applications in organic synthesis (175 references).

369 citations

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Abstract: Glycals (1,2-unsaturated, cyclic carbohydrate derivatives) readily undergo (catalyzed) substitution reactions at C-1 accompanied by allylic rearrangement. This reaction, currently named Ferrier rearrangement, or the Ferrier I reaction, has established itself as a useful synthetic tool for carbohydrate transformations. By means of this reaction, glycals can be converted into highly useful 2,3-unsaturated glycosides. This review summarizes recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals.

96 citations

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Abstract: Esterification of starch was carried out to expand the usefulness of starch for a myriad of industrial applications. Lipase obtained from Candida rugosa (lipase AYS) was used for starch esterification by two methods: liquid state and microwave oven. The esterification of cassava starch with recovered coconut oil (lauric acid) using microwave heating gave a degree of substitution of 55.28% with degree of substitution (DS) 1.1 and liquid state esterification with palmitic acid gave a degree of substitution of 65.86% with DS 1.04. Esterification was confirmed by IR spectroscopy studies. Thermal gravimetric analysis (TGA) showed that the higher DS attributed to the thermostability, since onset of decomposition is at a higher temperature (390 °C) than the unmodified (280 °C) and was stable above 600 °C. α-Amylase digestibility was found to be reduced for modified starch compared to the control (76.5–4.6%). Viscosity differed with the acyl donor used, palmitic acid increased viscosity while hydrolysed coconut oil reduced viscosity of modified starch ester. Esterification of starch with long chain fatty acids like palmitic acid gives thermoplastic starch which has got wide use in plastic industry, pharmaceutical industries, and in biomedical applications such as materials for bone fixation and replacements, carriers for controlled release of drugs and other bioactive agents. Unlike chemical esterification, enzymatic esterification is ecofriendly and avoids the use of nasty solvents.

72 citations


References
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Abstract: Four different types of organic reactions have been studied and seven different organic compounds have been prepared, under pressure in a microwave oven. Considerable rate increases have been observed.

1,428 citations

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Abstract: Commercial microwave ovens have been safely used to dramatically reduce the reaction times (at comparable yield) of Diels-Alder, Claisen, and ene reactions. Significant solvent effects were also observed.

983 citations

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Abstract: (1991). APPLICATIONS OF MICROWAVE ENERGY IN ORGANIC CHEMISTRY. A REVIEW. Organic Preparations and Procedures International: Vol. 23, No. 6, pp. 683-711.

380 citations

Journal ArticleDOI

329 citations