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Cycloaddition Reactions: MO Requirements for Photochemical Activation

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

Pericyclic Reactions: Introduction

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...

Cycloaddition Reactions: Overview

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.

The Photochemical Reaction Center

The Photochemical Reaction Center

Reaction centers are pigment-protein complexes that initiate energy conversion from photons to chemical entities. Therefore, photochemical reaction center is a more appropriate term that describes these complexes. The Nobel laureates Robert Emerson and William Arnold provided the first experimental evidence of photochemical reaction centers by demonstrating the participation of nearly 2,500 chlorophyll molecules for the release of just one molecule of oxygen. Despite thousands of photosynthetic...

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Multiple-cycle photochemical cascade reactions.

Dong Liang¹, Quan-Quan Zhou², Jun Xuan³

¹School of Chemistry and Materials Engineering, Fuyang Normal University, Fuyang 236037, China.

Organic & Biomolecular Chemistry

|February 22, 2024

Summary

This summary is machine-generated.

Visible-light-induced cascade reactions offer an efficient method for synthesizing complex organic molecules. This review highlights recent advancements in these photochemical reactions and their catalytic cycles.

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Area of Science:

Organic Chemistry
Photochemistry
Synthetic Chemistry

Background:

Cascade reactions enable efficient synthesis of complex organic compounds.
Photochemical reactions provide access to radical species under mild conditions.
Combining these strategies yields novel molecular structures.

Purpose of the Study:

To review recent advancements in visible-light-induced cascade reactions.
To elucidate photochemical catalytic cycles and activation modes.
To highlight the synthesis of complex molecules challenging under thermal conditions.

Main Methods:

Summarizing recent pivotal advancements in the field.
Analyzing multiple photochemical catalytic cycles.
Focusing on catalytic activation modes and reaction types.

Main Results:

Significant strides in photochemical cascade reactions have been made.
Novel molecular structures are now accessible.
Controlled synthesis under mild conditions is achievable.

Conclusions:

Visible-light-induced cascade reactions are a powerful synthetic tool.
These reactions enable the efficient construction of complex molecular architectures.
Further exploration of catalytic cycles promises new synthetic possibilities.