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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
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Cycloaddition Reactions: Overview01:16

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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.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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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.
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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
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Repurposing π Electrophilic Cyclization/Dealkylation for Group Transfer.

Joseph A Kaplan1, Adena Issaian1, Martin Stang1

  • 1Department of Chemistry, University of California, Irvine, Irvine, CA, 02697, USA.

Angewandte Chemie (International Ed. in English)
|September 29, 2021
PubMed
Summary

A new metal-free thioboration reaction creates trisubstituted alkenes with high regio- and stereocontrol. This efficient synthesis method offers predictable control over alkene structure for diverse applications.

Keywords:
alkene synthesisborylationborylative heterocyclizationmechanistic chemistry

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Trisubstituted alkenes are crucial building blocks in organic synthesis.
  • Developing regio- and stereoselective synthetic methods for these compounds remains a challenge.

Purpose of the Study:

  • To describe a novel metal-free group-transfer route for synthesizing trisubstituted alkenes.
  • To achieve regio- and stereocontrolled synthesis of complex alkenes from simple precursors.

Main Methods:

  • Electrophilic heterocyclization followed by ring-opening group transfer.
  • Thioboration reaction using B-chlorocatecholborane (ClBcat) with alkynyl sulfide precursors.

Main Results:

  • Successfully synthesized alkenyl boronates and alkenyl sulfides with defined regio- and stereochemistry.
  • Demonstrated that the stereochemistry is preserved from the initial cyclization to the final product.
  • Showcased downstream functionalization, highlighting the versatility of the synthesized alkenes.

Conclusions:

  • The developed thioboration reaction provides a powerful and predictable route to trisubstituted alkenes.
  • The mechanistic insights suggest broader applicability for designing new electrophilic heterocyclization/dealkylation sequences.