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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Amines to Alkenes: Cope Elimination01:14

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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
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Preparation of Epoxides03:00

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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Avenue to phosphaalkenes from Ph3GePCO.

Kevin M Szkop1, Andrew R Jupp, Hlib Razumkov

  • 1Department of Chemistry, University of Toronto, 80 St George St., Toronto, ON M5S 3H6, Canada. douglas.stephan@utoronto.ca.

Dalton Transactions (Cambridge, England : 2003)
|December 21, 2019
PubMed
Summary

New phosphaalkene isomers were synthesized from germylphosphinidene precursors. These isomers interconvert and undergo exchange reactions, suggesting a reversible silylphosphination mechanism.

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Area of Science:

  • Organometallic chemistry
  • Phosphorus chemistry
  • Silicon chemistry

Background:

  • Germylphosphinidene (Ph3GePCO) is a reactive intermediate.
  • Phosphaalkenes are compounds containing a carbon-phosphorus double bond.

Purpose of the Study:

  • To synthesize and characterize new phosphaalkene isomers.
  • To investigate the reactivity and isomerization mechanisms of these phosphaalkenes.

Main Methods:

  • Reaction of Ph3GePCO with KP(t-Bu)2 and Ph3SiCl.
  • Direct reaction with silylphosphine Ph3SiP(t-Bu)2.
  • Thermal and photochemical isomerization studies.
  • Silyl and phosphide exchange experiments.

Main Results:

  • Synthesis of (Z)- and (E)-isomers of (t-Bu2)PC(OSiPh3)P(GePh3) (2).
  • Isomers interconvert thermally and photochemically.
  • Compound 2 undergoes silyl and phosphide exchange with silylphosphines.

Conclusions:

  • The observed isomerization and exchange reactions are consistent with a mechanism involving reversible silylphosphination of Ph3GePCO.
  • This study expands the understanding of phosphaalkene chemistry and reactivity.