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Sunday, July 26, 2020 | History

2 edition of Rearrangements of secondary methylenecyclopropyl amides. found in the catalog.

Rearrangements of secondary methylenecyclopropyl amides.

Christina Schwarz

Rearrangements of secondary methylenecyclopropyl amides.

by Christina Schwarz

  • 220 Want to read
  • 35 Currently reading

Published .
Written in English


About the Edition

The mechanisms of both ring-expansion reactions were investigated extensively, employing deuterium labelled methylenecyclopropyl amide substrates.The magnesium iodide-mediated ring expansions of secondary methylenecyclopropyl amides have been examined in detail. The scope of the previously reported rearrangement reaction has been successfully extended, permitting the synthesis of a library of heteroaryl-substituted 4-methyl-1,5-dihydro-pyrrol-2-ones. Development of a novel, complimentary synthetic procedure enabled access to the isomeric 4-methylene-pyrrolidin-2-one products.

Edition Notes

ContributionsUniversity of Toronto. Dept. of Chemistry.
The Physical Object
Pagination124 leaves.
Number of Pages124
ID Numbers
Open LibraryOL19512341M
ISBN 100612952312

The Curtis rearrangement also involves the loss of one carbon (like the Hofmann rearrangement) but the reagents are ____ Amide Primary and secondary amines can by acylated with an acid chloride or acid anhydride to yield an ____. John H. MacMillan ([email protected]) Department of Chemistry Temple University, Philadelphia, Pa. p-Alkyl substituted anilines such as p-(trans-heptylcyclohexyl)aniline, quickly convert to secondary amides in high yield when treated with acid chlorides in toluene or procedure is applicable for preparing a wide variety of secondary amides from aromatic amines.

All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides with excellent functional group compatibility within short reaction time at rt. S. L. Zultanski, J. Zhao, S. S. Stahl, J. Am. Chem. Soc., , , Brønsted acid catalysis enables a synthesis of secondary amides from ketones under mild conditions via transoximation and Beckmann rearrangement. In this reaction, O-protected oximes serve as more stable equivalents of explosive O-protected hydroxylamines. This method can be used for amide synthesis from α-branched alkyl aryl ketones.

A tandem TBAB-catalyzed substitution and a subsequent novel oxidative rearrangement allow the synthesis of aryl or alkenyl nitriles from from benzyl and allyl halides. The broad reaction scope and the mild conditions may make these methods of use in organic synthesis. W. Zhou, J. Xu, L. Zhang, N. Jiao, Org. Lett., , 12, In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula RC(=O)NR′R″, where R, R′, and R″ represent organic groups or hydrogen atoms.. The amide group is called a peptide bond when it is part of the main chain of a protein, and isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine.


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Rearrangements of secondary methylenecyclopropyl amides by Christina Schwarz Download PDF EPUB FB2

Ring expansion of secondary methylenecyclopropyl amides in the presence of MgI 2 was investigated. Various isomeric five-membered unsaturated lactams were obtained, depending on the character of the substituent Q.

The amide group served as a nucleophile in ring closing as well as an activator for ring by: Ring expansion of secondary methylenecyclopropyl amides in the presence of MgI 2 was investigated.

Various isomeric five-membered unsaturated lactams were obtained, depending on the character of the substituent Q. The amide group served as a nucleophile in ring closing as well as an activator for ring opening. Synthesis of β,γ-Unsaturated Lactams via a Magnesium Iodide Promoted Ring Expansion of Secondary Methylenecyclopropyl Amides.

Organic Letters8 (24), DOI: /ol Fay W. Ng, Hong Lin, and, Samuel J. by: 4. Synthesis of Secondary Amides from. ‐Substituted Amidines by Tandem Oxidative Rearrangement and Isocyanate Elimination.

Pradip Debnath. Organic Synthesis, Department of Chemistry, University of Antwerp, GroenenborgerlaanB‐ Antwerp, Belgium, Fax: (+32)‐ (0)3‐‐; phone: (+32)‐ (0)3‐‐Cited by: The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals.

Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH).Author: Dinesh Chandra, Saumya Verma, Chandra Bhan Pandey, Ajay K. Yadav, Puneet Kumar, Bhoopendra Tiwari, J.

Conformational Features of Secondary N -Cyclopropyl Amides Article in The Journal of Organic Chemistry 80(8) March with Reads How we measure 'reads'. The rearrangement is stereospecific and the configuration at the migrating carbon is retained (see Section F).

The rearrangement product is called an isocyanate and is a nitrogen analog of a ketene (R 2 C = C = O); like ketenes, isocyanates readily add water.

A novel and efficient route to exo-β,γ-unsaturated lactams from substituted and non-substituted secondary methylenecyclopropyl amides is reported. Subsequent modification of the resulting exo-β,γ-unsaturated lactams provides access to several pharmaceutically relevant by: Synthesis of β,γ-Unsaturated Lactams via a Magnesium Iodide Promoted Ring Expansion of Secondary Methylenecyclopropyl Amides Mark E.

Scott, Christina A. Schwarz, and Mark Lautens Organic Letters 8 (24), Cited by: 3. [Ir(Cp*)Cl 2] 2 catalyzes the rearrangement of oximes to furnish amides. An iridium-catalyzed transfer hydrogenation between alcohols and styrene and the subsequent formation of an oxime allows the conversion of alcohols into amides in a one-pot process.

Owston, A. Parker, J. Williams, Org. Lett.,9, Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form –NH 2, –NHR, or –NRR′, where R and R′ are groups other than hydrogen.

The core –C (=O)N= of amides is called the amide group (specifically, carboxamide group). Amides. A secondary (2°) amide is an amide in whose molecule the nitrogen atom is bonded to two carbon atoms. eg: See also primary amide and tertiary amide.

Similarly to Py's method, intermediate lactams have previously been prepared by indium-catalyzed Conia-ene reactions [], by the selective ring expansion of secondary methylenecyclopropyl amides.

Molecular Rearrangements CH’Course’on’Organic’Synthesis;’Course’Instructor:’KrishnaP.’Kaliappan’. Migration of one group from one atom to another within the molecule. Generally the migrating group never leaves the molecule. There are five types of skeletal rearrangements- 1.

Cyclization reactions of propargylic amides, due to their rapid assembly of structural complexity and good functional group compatibility, have gained considerable attention in recent years. These transformations have been successfully achieved with transition metals, halogen sources, Bronsted acids, and strong by: Background: Amide bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds.

The Beckmann rearrangement is a well-known method used for the preparation of secondary amides from by: 1. Amide bond formation reactions are among the most important transformations in organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds.

The Beckmann rearrangement is a well-known method to generate secondary amides from ketoximes. Secondary amides and thioamides can undergo tautomeric equilibria, which provide for a variety of potential linkage isomers in their transition metal complexes [3,4].Amides usually bond with transition metal ions in their amidate (deprotonated) form, while their host–guest chemistry usually utilizes the hydrogen bond donating capabilities of the amide NH group in the neutral amide form (Fig.

Rearrangements • An unsubstituted amide can be converted to a primary amine by formal loss of the amide carbonyl through the Hofmann rearrangement (also called the Hofmann degradation) • The first two steps of the mechanism result in N-bromination of the amide – The N-bromoamide is deprotonated and rearranges to an isocyanateFile Size: 4MB.

Names of Secondary and Tertiary Amides 5 In the naming of secondary and tertiary amides, the alkyl groups on nitrogen are treated as substituents, and their position is specified by the prefix N- to differentiate them from any substituents located on the parent chain of the parent carboxylic acid.

The Chemistry of Amines - Section 23 of Organic Chemistry Notes is 19 pages in length (page through page ) and covers ALL you'll need to know on the following lecture/book topics: SECTION 23 - Amines -- Primary (1°), Secondary (2°), and Tertiary (3°) Amines -- .• Amides possess a functional group that consists of a C=O (carbonyl) directly bound to a nitrogen: • The amide functional group involves a nitrogen atom (and lone pair), but unlike an amine, the nitrogen center is not basic, due to the electron-withdrawing effect of the C=O group.

For amides, R, R’, and R” can be • carbon-based, or.The combination of amide activation by Tf 2 O with B(C 6 F 5) 3-catalyzed hydrosilylation with TMDS enables a one-pot reduction of secondary amides to amines under mild conditions with broad applicability and excellent chemoselectivity for many sensitive functional groups.