Intramolecular Diels Alder And Alder Ene Reactions
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Intramolecular Diels Alder And Alder Ene Reactions
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Author : Douglass F. Taber
language : en
Publisher: Springer Science & Business Media
Release Date : 2012-12-06
Intramolecular Diels Alder And Alder Ene Reactions written by Douglass F. Taber and has been published by Springer Science & Business Media this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012-12-06 with Science categories.
The Diels-Alder reaction has long been a powerful tool in organic synthesis. In recent years, the Alder ene reaction has also achieved some prominence. From the beginning, it was apparent that the intramolecular variants of these reactions would be feasible. Many such have been reported, but the results are widely scattered in the chemical literature. This volume is an attempt to synthesize results observed to date, and to suggest directions for future development. One of the limiting factors in the application of the intramolecular Diels Alder reaction has been the development of methods for the preparation of the requisite trienes. The fIrst chapter of this volume summarizes methods for the preparation of dienes and dienophiles. Examples representative of every general approach to 1,3-dienes and to dienophilic functional group combinations have been included. There are two questions one might ask in considering the prospective cyclization of a given triene: what are the factors that govern the rate of cyclization? and, for cyclizations that lead to the creation of one or more new chiral centers, what are the factors that govern diastereoselectivity? These questions are addressed in Chapter Two. The third chapter is devoted to the all-carbon intramolecular Alder ene reaction. The tables in that chapter summarize all examples that could be found in the literature through 1981, with several additional examples from 1982. Leading references to heterocyclic ene reactions are also included in this chapter.
Intramolecular Diels Alder And Alde Ene Reactions
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Author : D. F. Taber
language : en
Publisher:
Release Date : 1984
Intramolecular Diels Alder And Alde Ene Reactions written by D. F. Taber and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 1984 with Diels-Alder reaction categories.
The Diels Alder Reaction
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Author : Francesco Fringuelli
language : en
Publisher: John Wiley & Sons
Release Date : 2002-01-21
The Diels Alder Reaction written by Francesco Fringuelli and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2002-01-21 with Science categories.
70 Jahre Forschung an der Diels-Alder-Reaktion: Dieses Buch fasst die wichtigsten und beeindruckendsten Ergebnisse in einzigartiger Weise zusammen! Zunächst werden die Grundprinzipien der Reaktion klar und verständlich anhand übersichtlicher Graphiken erläutert. Spezielle Vorschriften und gegebenenfalls ihre industrielle Umsetzung werden anschließend erklärt. Einen Schwerpunkt bilden auch physikalische und katalytische Verfahren zur Steigerung der Selektivität der Reaktion. Cycloadditionen in konventionellen und unkonventionellen Medien werden vorgestellt. Mit über 1.000 Literaturverweisen!
Stereoselective And Regioselective Lewis Acid Catalyzed Ene Reactions
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Author : John Jonas Vytautas Dunčia
language : en
Publisher:
Release Date : 1982
Stereoselective And Regioselective Lewis Acid Catalyzed Ene Reactions written by John Jonas Vytautas Dunčia and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 1982 with categories.
Cycloaddition Reactions In Organic Synthesis
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Author : W. Carruthers
language : en
Publisher: Elsevier
Release Date : 2013-10-22
Cycloaddition Reactions In Organic Synthesis written by W. Carruthers and has been published by Elsevier this book supported file pdf, txt, epub, kindle and other format this book has been release on 2013-10-22 with Science categories.
Demonstrates the wide scope of cycloaddition reactions, including the Diels-Alder reaction, the ene reaction, 1,3-dipolar cycloadditions and [2+2] cycloadditions in organic synthesis. The author, a leading exponent of the subject, illustrates the ways in which they can be employed in the synthesis of a wide range of carbocyclic and heterocyclic compounds, including a variety of natural products of various types. Special attention is given to intramolecular reactions, which often provide a rapid and efficient route to polycyclic compounds, and to the stereochemistry of the reactions, including recent and developing work on enantioselective synthesis.
Intramolecular Diels Alder Reactions In Organic Synthesis
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Author : Nicholas Blandford Luke Sizemore
language : en
Publisher:
Release Date : 2014
Intramolecular Diels Alder Reactions In Organic Synthesis written by Nicholas Blandford Luke Sizemore and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2014 with categories.
Intramolecular Diels-Alder (IMDA) reactions are an important class of reactions in synthetic organic chemistry for the rapid construction of polycyclic frameworks. Three classes of IMDA reactions were investigated synthetically and computationally: 1) all-carbon type 1 IMDA reactions, 2) N-acylnitroso type 2 IMDA reactions, and 3) cyano-azadiene IMDA reactions. The first class was implemented in research toward the total synthesis of maoecrystal Z and isopalhinine A. The second class was studied computationally to understand the origins of regio- and stereochemistry in these reactions. The third class was investigated in the context of indolizine and quinolizidine synthesis.
A Deeper Understanding Of The Diels Alder Reaction
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Author : William James Lording
language : en
Publisher:
Release Date : 2010
A Deeper Understanding Of The Diels Alder Reaction written by William James Lording and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2010 with Diels-Alder reaction categories.
The Diels-Alder reaction was discovered in 1928 and has become the most efficient and practical method for the synthesis of six-membered carbocyclic and heterocyclic rings. This thesis comprises three chapters of results and discussion with the Diels-Alder reaction as a theme. Chapter 2 details an investigation of endo:exo selectivity in the Diels-Alder reactions of 1,3-butadiene. Chapter 3 explores aspects of the intramolecular Diels-Alder reactions of some substituted 1,3,8-nonatrienes, and Chapter 4 describes the domino Diels-Alder reactions of 1,4-diiodo-1,3-butadiene. The Diels-Alder reaction is powerful, general, and widely used in chemical synthesis, and it is well known that many Diels-Alder reactions exhibit endo selectivity, in accord with Alder's empirical rule. The origins of endo:exo selectivity in the Diels-Alder reaction, however, are not completely understood and there is a dearth of experimental evidence concerning the Diels-Alder reactions of the archetypal 1,3-diene, 1,3-butadiene. Chapter 2 describes a study of the Diels-Alder reactions of an isotopically labelled 1,3-butadiene with a range of simple dienophiles, allowing the endo:exo selectivities of these important reactions to be determined for the first time. The experimental data shed light on the origins of endo:exo selectivity in the Diels-Alder reaction and will serve as an important reference for future computational investigations in this area. The intramolecular Diels-Alder reaction shares many of the virtues of its intermolecular counterpart, however its use in chemical synthesis is limited because intramolecular Diels-Alder reactivity and stereoselectivity are often governed by subtle factors, and can be very difficult to predict. As part of a comprehensive experimental and computational collaboration, Chapter 3 describes an investigation of the heat and Lewis acid promoted intramolecular Diels-Alder reactions of some ether tethered 1,3,8-nonatrienes. Also presented are the results of a rate study and a kinetic isotope effect study involving the intramolecular Diels-Alder reactions of some 1,3,8-nonatrienes. The experimental data are analysed and compared with predicted stereoselectivities, activation barriers and kinetic isotope effects obtained from computational modelling. Increased efficiency in chemical synthesis conserves resources, reduces waste, and saves time and money. Domino reactions are particularly efficient processes, which can generate complex products from simple reactants. Chapter 4 describes an investigation of the domino Diels-Alder reactions of (1E,3E)-1,4-diiodo-1,3-butadiene with maleimide dienophiles, through which a family of bicyclo[2.2.2]oct-2-ene derivatives are produced in one high yielding and stereoselective synthetic step.
Dienes In The Diels Alder Reaction
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Author : Francesco Fringuelli
language : en
Publisher: Wiley-Interscience
Release Date : 1990-05-31
Dienes In The Diels Alder Reaction written by Francesco Fringuelli and has been published by Wiley-Interscience this book supported file pdf, txt, epub, kindle and other format this book has been release on 1990-05-31 with Science categories.
Dealing with the intermolecular Diels-Alder reaction, this book focuses on one of the reactants - the diene. Following an examination of the fundamental principles of the reaction are descriptions of the salient features of the different classes of dienes.
Theoretical Studies Of The Diels Alder Reaction And The Alder Ene Reaction
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Author : Richard James Loncharich
language : en
Publisher:
Release Date : 1987
Theoretical Studies Of The Diels Alder Reaction And The Alder Ene Reaction written by Richard James Loncharich and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 1987 with Diels-Alder reaction categories.
Studies On The Intramolecular Diels Alder Reaction
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Author : Geoff T. Halvorsen
language : en
Publisher:
Release Date : 2012
Studies On The Intramolecular Diels Alder Reaction written by Geoff T. Halvorsen and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012 with Diels-Alder reaction categories.
The intramolecular Diels-Alder reaction is widely recognized as a powerful and versatile method for the assembly of complex bicyclic structures in synthetic organic chemistry and has been utilized as a key step in the total syntheses of a number of interesting biologically active natural products. We have studied the use of siloxacyclopentene constrained trienes as a method to control diastereofacial selectivity in the intramolecular Diels-Alder reaction. The siloxacyclopentene constraints could be formed under mild conditions and attached to either the diene or dienophile units of a variety of trienes. These constrained trienes underwent intramolecular Diels-Alder reactions to give cycloadducts with the oxygen contained in the siloxacyclopentene exclusively in an anti-configuration relative to the ring fusion proton. Suitably chosen dienophile activating groups and optimized conditions for cyclization allowed for high levels of selectivity for either cis - or trans -fused cycloadducts in the case of siloxacyclopentenes contained within the diene, while siloxacyclopentenes constraints attached at the dienophile gave exclusively the trans-fused cycloadducts. A siloxacyclopentene constrained tetraene was then utilized in a concise, stereoselective synthesis of the decahydrofluorene core common to the hirsutellones. Synthetic efforts targeting the completion of the hirsutellones via a common biosynthetic intermediate were pursued utilizing a macrobenzannulation strategy. This strategy was abandoned due to inability to prepare a suitable benzannulation precursor. Later a strategy of first forming a five membered ring containing analogue was also pursued, but failed due to an inability to convert a suitable ester to the corresponding furan or thiophene.