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Intramolecular reaction

About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.


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TL;DR: Intramolecular Diels-Alder reactions involving a series of N-alkenyl-substituted furanyl amides were investigated, and stable functionalized oxanorbornenes were formed in high yield upon heating at 80-110 degrees C.
Abstract: Intramolecular Diels−Alder reactions involving a series of N-alkenyl-substituted furanyl amides were investigated. Stable functionalized oxanorbornenes were formed in high yield upon heating at 80−110 °C. The cycloaddition reactions include several bromo-substituted furanyl amides, and these systems were found to proceed at a much faster rate and in higher yield than without substitution. This effect was observed by incorporating a halogen in the 3- or 5-position of the furan ring and appears to be general. The origin of increased cycloaddition rates for halo-substituted furans has been investigated with quantum mechanical calculations. The success of these reactions is attributed to increases in reaction exothermicities; this both decreases activation enthalpies and increases barriers to retrocycloadditions. Halogen substitution on furan increases reactant energy and stabilizes the product, which is attributed to the preference of electronegative halogens to be attached to a more highly alkylated and the...

48 citations

Journal ArticleDOI
TL;DR: An improved synthesis into the oxazepine and thiazepine ring systems is disclosed, which exploits recent advancements in the palladium-catalyzed amination reaction to form the seven-membered rings.
Abstract: Azaheterocyclic compounds are interesting and medicinally relevant targets. Herein we disclose an improved synthesis into the oxazepine and thiazepine ring systems. The key step in the synthesis exploits recent advancements in the palladium-catalyzed amination reaction, which was utilized to form the seven-membered rings. General conditions for this reaction were Pd2dba3, P(t-Bu)3, NaO-t-Bu alone or with K2CO3, in toluene. The scope of the reaction was investigated, and has been shown to be effective on a variety of substrates as illustrated.

48 citations

Journal ArticleDOI
TL;DR: In this article, the effect of monomer structure and catalyst on the synthesis of hyperbranched polyesters based on 4,4-(4′-hydroxyphenyl)pentanoic acid has been examined.
Abstract: The effect of monomer structure and catalyst on the synthesis of hyperbranched polyesters based on 4,4-(4′-hydroxyphenyl)pentanoic acid has been examined. The nature of the ester group and the catalyst have a significant effect on the molecular weight of the hyperbranched polyester but do not effect the degree of branching for these materials. The fate of the single ester group at the focal point of these hyperbranched macromolecules is probed by the synthesis and polymerization of 13C labeled methyl 4,4-(4′-hydroxyphenyl)pentanoate. Comparison of the molecular weights determined by 1H- or 13C-NMR spectra with those determined by osmometry suggest that intramolecular cyclization does not occur to a significant extent in these systems. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 1627–1633, 1997

48 citations

Journal ArticleDOI
TL;DR: In this paper, 2-butenylene dicarbonate with dimethyl malonate and methyl acetylacetate in the presence of a chiral ferrocenylphosphine-palladium catalyst gave optically active dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (70% ee) and methyl 2-methyl-5-methyl -4,5 -vinyl-4, 5-dihydrofuran-3-carboxylates (59% Ee), respectively

48 citations

Journal ArticleDOI
TL;DR: In this article, dissaccharides containing 1,2-cis glycoside linkages were synthesized by an efficient stereocontrolled two-step process involving a silicon tethering step, to a dimethylsilyl acetal followed by intramolecular glycosidation with N-iodosuccinimide in nitromethane.

48 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20231
20228
20216
202011
20199
20186