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Related Concept Videos

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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Functionalization reactions characteristic of a robust bicyclic diphosphane framework.

Daniel Tofan1, Manuel Temprado, Subhojit Majumdar

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Inorganic Chemistry
|July 12, 2013
PubMed
Summary

The novel 3,4,8,9-tetramethyl-1,6-diphospha-bicyclo-[4.4.0]deca-3,8-diene framework enables selective functionalization of diphosphane molecules. This allows for controlled synthesis of diverse phosphorus compounds and metal complexes.

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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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Synthesis and Characterization of Functionalized Metal-organic Frameworks

Published on: September 5, 2014

Area of Science:

  • Organophosphorus Chemistry
  • Coordination Chemistry
  • Synthetic Chemistry

Background:

  • Acyclic diphosphanes often undergo non-selective functionalization.
  • The unique bicyclic diphosphane framework offers new possibilities for controlled reactivity.

Purpose of the Study:

  • To explore the selective functionalization of the 3,4,8,9-tetramethyl-1,6-diphospha-bicyclo-[4.4.0]deca-3,8-diene framework.
  • To synthesize novel diphosphane chalcogenides, iminophosphoranes, and their metal complexes.
  • To investigate the reactivity and properties of these new organophosphorus compounds.

Main Methods:

  • Selective reaction of the diphosphane with chalcogen-atom donors (MesCNO, SSbPh3).
  • Reactions with azides to form mono- and diiminophosphoranes.
  • Metalation reactions with bulky diiminodiphosphorane ligands and transition metals (Mo, Ni).
  • Calorimetric studies for bond dissociation enthalpies and computational studies.

Main Results:

  • Selective synthesis of diphosphane chalcogenides (mono- and di-oxides/sulfides) with high yields.
  • Isolation of mono- and diiminophosphoranes, including symmetric and unsymmetric derivatives.
  • Characterization of novel transition metal complexes with diiminodiphosphorane ligands.
  • Measured P-O and P-S bond dissociation enthalpies in good agreement with computed values.

Conclusions:

  • The bicyclic diphosphane framework allows for unprecedented selectivity in functionalization.
  • This selectivity enables the synthesis of diverse organophosphorus compounds with potential applications in coordination chemistry.
  • The diiminodiphosphorane ligands form stable complexes with transition metals, highlighting their utility as preorganized binding pockets.