Formal [1,3] rearrangement of 2-furylmethyl and 2-thienylmethyl vinyl ethers
TL;DR: For example, 2-furyl and 2-thicnylmelhyl vinyl ethers undergo formal [1,3] rearrangement in LPDE medium as discussed by the authors.
About: This article is published in Tetrahedron Letters.The article was published on 1995-12-25. It has received 11 citations till now.
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TL;DR: In this article, the tetrahydropyranyl ethers were obtained in the presence of 5 M lithium perchlorate in diethyl ether (5 M LPDE), which is essentially a neutral medium.
50 citations
29 citations
TL;DR: This work reviews the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules.
Abstract: The Claisen rearrangement of benzylic substrates (benzyl vinyl ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules. 1 Introduction 2 Early Attempts at the Benzyl-Claisen Rearrangement 3 Successful Benzylic Examples 4 Heterobenzylic Examples 5 Conclusion
11 citations
TL;DR: In this article, two reactions, vinyl polymerization and [1,3] O to C rearrangement of vinyl ethers, are investigated in the ruthenium-catalyzed reaction with hydrosilanes.
11 citations
TL;DR: In this article, the effect of increase of polarity of the solvent binary mixture methanol-benzene and acetonitrile-chloroform on the selectivity and the rate of metalloene reaction of different allyltin compounds with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), diethyl azodicarboxylate (DEAD) and singlet oxygen was studied.
9 citations
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01 Jan 1985TL;DR: The Handbook of Heterocyclic Chemistry as discussed by the authors has been updated with over 50% new content, including a new expanded author team, who have carefully distilled essential information on the reactivity, structure and synthesis of heterocycles.
Abstract: Heterocyclic compounds play a vital role in the metabolism of living cells. Their practical applications range from extensive clinical use to fields as diverse as agriculture, photography, biocide formulation and polymer science. Written by leading scholars and industry experts, the Handbook of Heterocyclic Chemistry is thoroughly updated with over 50% new content. It has been rewritten with a new expanded author team, who have carefully distilled essential information on the reactivity, structure and synthesis of heterocycles from the 2008 major reference work Comprehensive Heterocyclic Chemistry III. To bring the work up to date the author team have also added new synthetic examples and structures, key applications and new references from 2008-2010. Contains more than 1500 clearly drawn structures and reactions. The highly systematic coverage given to the subject makes this one of the most authoritative single-volume accounts of modern heterocyclic chemistry available and should be useful reference for those teaching a heterocyclic course. -Covers the structure, reactivity and synthesis of all heterocyclic compounds as distilled from the larger 15-volume reference work -Saves researchers time when they require important information on heterocycles--speeding them to thousands of clearly drawn chemical structures and pertinent reviews by leading experts -Features 35% new material to compliment the completely revised text
727 citations
108 citations
TL;DR: In this paper, the glycosyl donors 2,3,4-tri-O-benzyl fucosyl fluoride and trichloroacetimidate are activated under neutral conditions in 1M solutions of LiClO 4 in CH 2 Cl 2 or ether to react with mono- and disaccharides to give fucoseyl glycosides in high yields and with high stereoselectivity.
36 citations
TL;DR: Allylic alcohols of type 1 undergo unprecedented substitution with O-silylated ketene acetals in 3.0 M lithium perchlorate-diethyl ether as discussed by the authors.
22 citations