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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Published on: October 3, 2014

Prototypical triplet alkyl phosphonatocarbenes.

Adelina Nemirowski1, Hans Peter Reisenauer, Jaroslaw Romanski

  • 1Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany.

The Journal of Physical Chemistry. A
|October 11, 2008
PubMed
Summary

Researchers generated and identified novel alkyl phosphonatocarbenes using matrix isolation and computational methods. These triplet ground-state carbenes showed stability and unique reactivity, leading to new compounds like methyl metaphosphate.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

  • Organophosphorus Chemistry
  • Carbene Chemistry
  • Computational Chemistry

Background:

  • Alkyl phosphonates are versatile compounds with diverse applications.
  • Carbenes are highly reactive intermediates crucial in organic synthesis.
  • Understanding carbene stability and reactivity is key to developing new synthetic pathways.

Purpose of the Study:

  • To synthesize and characterize mono- and disubstituted alkyl phosphonatocarbenes.
  • To investigate the electronic structure and stability of these novel carbene species.
  • To explore the reactivity and fragmentation pathways of alkyl phosphonatocarbenes.

Main Methods:

  • Matrix isolation techniques for carbene generation and stabilization.
  • Electron Paramagnetic Resonance (EPR) spectroscopy for characterization.
  • Density Functional Theory (DFT) and Coupled Cluster (CC) computational methods for theoretical analysis.

Main Results:

  • Successful generation and identification of two representative alkyl phosphonatocarbenes.
  • EPR measurements confirmed triplet ground states for both carbenes.
  • Observed stability of carbenes towards intramolecular reactions up to 70 K.
  • Tetramethyl bisphosphonatocarbene reacted to form phosphaoxetane and fragmented into dimethyl vinylphosphonate and methyl metaphosphate.
  • Methyl metaphosphate was isolated as a novel entity.

Conclusions:

  • Alkyl phosphonatocarbenes can be generated and characterized using combined experimental and computational approaches.
  • These carbenes exhibit significant stability and unique reactivity patterns.
  • The study provides new insights into organophosphorus chemistry and carbene reaction mechanisms, including the first isolation of methyl metaphosphate.