Rearrangements in Ground and Excited States

Rearrangements in Ground and Excited States

Organic Chemistry: A Series of Monographs, Vol. 3

1st Edition - January 28, 1980

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  • eBook ISBN: 9781483218731

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Rearrangements in Ground and Excited States, Volume 3 presents essays on the chemical generation of excited states; the cis-trans isomerization of olefins; and the photochemical rearrangements in trienes. The book also includes essays on the zimmerman rearrangements; the photochemical rearrangements of enones; the photochemical rearrangements of conjugated cyclic dienones; and the rearrangements of the benzene ring. Essays on the photo rearrangements via biradicals of simple carbonyl compounds; the photochemical rearrangements involving three-membered rings or five-membered ring heterocycles; and the photochemical rearrangements of coordination compounds are also covered. Chemists and people involved in the study of the rearrangements in ground and excited states will find the book invaluable.

Table of Contents

  • List of Contributors

    Contents of Other Volumes

    Essay 13 Chemical Generation of Excited States

    I. Introduction

    II. Thermal Generation of Excited Carbonyls: Thermal Fragmentation of Dioxetanes

    III. Thermolysis of Peroxides: Chemical Generation of Molecular Oxygen

    IV. Chemiluminescent Pericyclic Rearrangements

    V. Applications of Chemiexcitation to Photochemical and Mechanistic Problems

    VI. Rearrangements to Produce Chemiluminescent Intermediates


    Essay 14 Cis- Trans Isomerization of Olefins

    I. Theoretical Considerations

    II. Thermal Cis-Trans Isomerization

    III. Thermochemical Cis-Trans Isomerization

    Note Added in Proof


    Essay 15 Photochemical Rearrangements in Trienes

    I. Introduction

    II. Photochemical Reactions

    III. Discussion and Results


    Essay 16 The Di-ir-Methane (Zimmerman) Rearrangement

    I. General Formulation of the Reaction: An Introduction

    II. The Gross Reaction Mechanism

    III. Reaction Multiplicity

    IV. Reaction Regioselectivity

    V. Role of the Second ð Bond

    VI. Reaction Stereochemistry

    VII. Structural Effects: Central Substitution and Conformation

    VIII. Substituent Effects

    IX. Barrelene-Related Examples

    X. Independent Generation of Cyclopropyldicarbinyl Diradicals

    XI. Additional Examples


    Essay 17 Photochemical Rearrangements of Enones

    I. General Introduction

    II. Photorearrangements of Cyclohex-2-en-l-ones

    III. Rearrangements of 2-Cyclopentenones and Related Compounds

    IV. Miscellaneous Rearrangements of a,0-Enones

    V. Photochemical Rearrangements of â,ã-Enones


    Essay 18 Photochemical Rearrangements of Conjugated Cyclic Dienones

    I. Rearrangements of Cross-Conjugated Dienones

    II. Rearrangements of Linearly Conjugated Dienones


    Essay 19 Rearrangements of the Benzene Ring

    I. Introduction

    II. Nonphotochemical Rearrangements of the Benzene Ring

    III. Photochemical Rearrangements of the Benzene Ring


    Essay 20 Photorearrangements Via Biradicals of Simple Carbonyl Compounds

    I. Introduction

    II. Cleavage Reactions

    III. Hydrogen Abstraction

    IV. Cycloadditions


    Essay 21 Photochemical Rearrangements Involving Three-Membered Rings

    I. Introduction

    II. Three-Membered Heterocycles with One Heteroatom

    III. Three-Membered Heterocycles with Two Heteroatoms

    IV. Three-Membered Heterocycles with Three Heteroatoms

    V. Conclusion


    Essay 22 Photochemical Rearrangements of Five-Membered Ring Heterocycles

    I. Introduction

    II. Mechanistic Possibilities for Photoisomerization of Five-Membered Heterocycles

    III. Five-Membered Ring Systems with One Heteroatom

    IV. Five-Membered Ring Systems with Two Heteroatoms References

    Essay 23 Photochemical Rearrangements of Coordination Compounds

    I. Introduction

    II. Photochemical Isomerizations of Coordination Compounds

    III. Stereochemical Changes during Ligand Photosubstitution: Chromium(III) Complexes



Product details

  • No. of pages: 622
  • Language: English
  • Copyright: © Academic Press 1980
  • Published: January 28, 1980
  • Imprint: Academic Press
  • eBook ISBN: 9781483218731

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