Regioselectivity of aryl radical attack onto isocyanates and isothiocyanates

Geethika K Weragoda1, Rowan L Pilkington, Anastasios Polyzos

  • 1CSIRO Manufacturing, Research Way, Clayton, VIC 3168, Australia.

Related Concept Videos

Acid Attack on Concrete01:21

Acid Attack on Concrete

When acids come into contact with concrete, they initiate a chemical reaction that dissolves the hydrated cement paste. This process leads to softening and structural weakening of the concrete. This issue is commonly observed in environments such as chimneys, sewers, and industrial settings. The severity of the damage increases as the pH of the water interacting with the concrete drops below 6.5. In particular, a pH under 4.5 can cause significant concrete damage.
The rate at which hydrogen...
757
Sulfate Attack on Concrete01:29

Sulfate Attack on Concrete

Sulfate attack on concrete is a deterioration process characterized by a whitish discoloration beginning at the edges and corners, accompanied by cracking and spalling. This phenomenon occurs when sulfates react with the components of hardened concrete, forming compounds like calcium sulfate and calcium sulfoaluminate which occupy more space than the substances they replace, causing the concrete to expand and disrupt.
Sulfates from sources like soil, groundwater, or industrial effluents...
742
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.2K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.5K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
3.5K