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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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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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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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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.
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sp3d and sp3d 2 Hybridization
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Introduction
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A Persistent 1,2-Dihydrophosphasilene Adduct.

Kerstin Hansen1, Tibor Szilvási2, Burgert Blom1,3

  • 1Department of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 135, Sekr. C2, 10623 Berlin (Germany).

Angewandte Chemie (International Ed. in English)
|October 21, 2015
PubMed
Summary

Researchers synthesized the first 1,2-dihydrophosphasilene adduct, a novel silicon-phosphorus compound. This adduct can be stabilized through tungsten complexation or silylation, revealing insights into silicon-phosphorus bonding.

Keywords:
heavier olefin analoguesmultiple bondsphosphorussiliconzwitterions

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Area of Science:

  • Organosilicon Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Silylenes, silicon analogs of carbenes, are reactive intermediates with unique bonding properties.
  • The synthesis and characterization of silicon-phosphorus compounds remain a challenge.

Purpose of the Study:

  • To synthesize and characterize novel 1,2-dihydrophosphasilene adducts.
  • To explore the stabilization strategies for these reactive species.
  • To investigate the electronic structure of the silicon-phosphorus bond.

Main Methods:

  • Reaction of an arylchlorosilylene-NHC adduct with LiPH2.
  • Stabilization via tungsten complexation and silylation.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • The first 1,2-dihydrophosphasilene adduct (ArSi(NHC)(H)PH) was synthesized.
  • The adduct can dimerize or be stabilized by complexation with a tungsten pentacarbonyl fragment.
  • A novel 1-silyl-2-hydrophosphasilene was also synthesized and characterized.
  • DFT studies revealed a zwitterionic Si-P bond with reduced double-bond character.

Conclusions:

  • Novel 1,2-dihydrophosphasilene adducts and their stabilized derivatives were successfully synthesized.
  • The study provides new insights into the reactivity and electronic structure of silicon-phosphorus compounds.
  • Tungsten complexation offers a viable route to stabilize these transient species.