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SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Copper-Catalyzed S-C/S-N Bond Interconversions.

Jian Wen1, Hanchao Cheng1, Shunxi Dong1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 20, 2016
PubMed
Summary
This summary is machine-generated.

Copper catalysts enable the synthesis of sulfonimidamides from unprotected sulfoximines using de-alkylation/amination. Radical mechanisms are proposed for C-S bond cleavage and N-S bond formation.

Keywords:
copperdemethylationoxygensulfonimidamidessulfoximines

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sulfur Chemistry

Background:

  • Sulfoximines are versatile synthetic intermediates.
  • Developing efficient methods for sulfonimidamide synthesis is crucial.

Purpose of the Study:

  • To develop a copper-catalyzed method for synthesizing sulfonimidamides.
  • To utilize unprotected sulfoximines as starting materials.

Main Methods:

  • Copper-catalyzed de-alkylation/amination reactions.
  • Reactions performed under an atmosphere of dioxygen.
  • Mechanistic studies to elucidate reaction pathways.

Main Results:

  • Sulfonimidamides were synthesized from unprotected sulfoximines in moderate to good yields.
  • The reaction sequence involved de-alkylation and amination.
  • Mechanistic studies indicated radical involvement in C-S and N-S bond formation.

Conclusions:

  • A novel copper-catalyzed route to sulfonimidamides from unprotected sulfoximines has been established.
  • The methodology offers a practical approach to accessing valuable sulfonimidamide structures.
  • Radical intermediates play a key role in the catalytic cycle.