Format:
Online-Ressource
,
graph. Darst.
Edition:
Online-Ausg. 2007 Springer eBook Collection. Chemistry and Materials Science Electronic reproduction; Available via World Wide Web
ISBN:
9783540490760
Content:
This book offers a systematic compilation of the vast data available to synthetic chemists. It provides easy access to the necessary information required for chemical transformations.
Content:
9-Borabicyclo [3.3.1]nonane, a commercially available reagent, is the most versatile hydroborating reagent to synthesize organoboranes (B-R-9-BBN). The reagent exhibits remarkable regio-, chemo-, and stereoselectivity during hydroboration reactions. The organoboranes can be converted to C-H, C-O, C-N, C-S, C-halogen, C-metal and above all C-C bonds. In addition, the suitable substituted / unsaturated R of B-R-9-BBN can be utilized to produce dienes, enynes, allenes etc. with defined stereochemistry. 9-BBN's derivatives have been elegantly used for the asymmetric reduction of ketone moiety. Die
Note:
Includes bibliographical references and index
,
CONTENTS; 1 Introduction; 2 General Remarks; 3 Preparation and Properties; 4 Kinetic Studies; 4.1 Hydroboration Kinetics of Alkenes; 4.2 Hydroboration Kinetics of Alkynes; 4.3 Hydroboration Kinetics of Haloalkenes; 4.4 Hydroboration Kinetics of Haloalkynes; 4.5 Reduction Kinetics; 4.6 Kinetics of Complex Formation; 4.7 Kinetics of Protonolysis; 5 Hydroboration; 5.1 Hydroboration of Alkenes; 5.2 Hydroboration of Alkynes; 5.3 Hydroboration of Dienes; 5.4 Hydroboration of Allenes; 5.5 Hydroboration of Enynes and Diynes; 6 Synthesis of Alcohols; 6.1 Synthesis of Saturated Alcohols
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6.2 Synthesis of Allylic Alcohols6.3 Synthesis of Homoallylic Alcohols; 6.4 Synthesis of Propargylic Alcohols; 6.5 Synthesis of Homopropargylic Alcohols; 6.6 Synthesis of Silyl Alcohols; 6.7 Synthesis of Heterocyclic Alcohols; 6.8 Synthesis of Amino Alcohols; 6.9 Asymmetric Synthesis of Alcohols; 7 Synthesis of Aldehydes and Ketones; 7.1 Synthesis of Aldehydes; 7.2 Synthesis of Ketones; 8 Synthesis of Carboxylic Acids; 8.1 Synthesis of Unsaturated Acids; 8.2 Synthesis of β-Amino Acids; 9 Synthesis of Esters; 9.1 Synthesis of Achiral Esters; 9.2 Synthesis of Chiral Esters
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9.3 Synthesis of (E)-β,γ-Unsaturated Esters9.4 Synthesis of α-Amino Acid Esters; 10 Synthesis of Nitriles; 10.1 Synthesis of Achiral Nitriles; 10.2 Synthesis of Chiral Nitriles; 10.3 Synthesis of (E)-β,γ-Unsaturated Nitriles; 11 Synthesis of (E)-β,γ-Unsaturated Amides; 12 Synthesis of Amines; 12.1 Synthesis of Chiral Amines; 12.2 Synthesis of Homopropargylic Amines; 12.3 Synthesis of Secondary Amines; 13 Synthesis of Halides; 13.1 Synthesis of Halides via Hydroboration; 13.2 Synthesis of Halides via Haloboration; 14 Synthesis of Dialkylsulfides; 15 Synthesis of Thiophene Oligomers
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16 Synthesis of Cyclopropanes and Cyclobutanes17 Synthesis of Borinanes; 18 Synthesis and Transformations of Butterflyboranes: cis-Bicyclo[3.3.0]oct-1-yldialkylboranes; 19 Synthesis of α-Bromoboranes; 20 Synthesis of Borinates; 20.1 Enol Borinates; 20.2 Synthesis of Alkynylborinates; 21 Synthesis and Transformation of Polymers; 22 Synthesis of Alkali Metal 9-Boratabicyclo [3.3.1] nonane (Li, K, and Na 9-BBNH); 23 Synthesis of B-R-9-BBN Not Available via Hydroboration; 24 Synthesis of Unsaturated Compounds; 24.1 Synthesis of Alkenes; 24.2 Synthesis of Dienes; 24.3 Synthesis of Enynes
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24.4 Synthesis of Endiynes25 Reduction; 25.1 With 9-BBN·THF; 25.2 With 9-BBN·Py; 25.3 With Li 9-BBNH; 25.4 With B-Siamyl-9-BBN; 25.5 With Lithium 9,9-Di-n-Butyl-9-Borabicyclo[3.3.1]nonanate; 25.6 With 9-BBN Derivatives (as Catalysts); 26 Asymmetric Reduction; 26.1 Alpine-Borane; 26.2 NB-Enantrane; 26.3 Eapine-Borane and Prapine-Borane; 26.4 NB-Enantride; 26.5 Eapine-Hydride; 26.6 K-Glucoride; 26.7 K-Xylide; 26.8 K9-OThx-9-BBNH; 26.9 Lithium Di-n-Butyl Ate Complex of 9-BBN; 26.10 Li 9-BBNH; 26.11 Comparative Data of Asymmetric Reducing Agents; 27 Cleavage of Ethers; 28 trans-Metalation
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29 Separation of Isomers
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CoverContents -- 1 Introduction -- 2 General Remarks -- 3 Preparation and Properties -- 4 Kinetic Studies -- 4.1 Hydroboration Kinetics of Alkenes -- 4.2 Hydroboration Kinetics of Alkynes -- 4.2.1 Relative Rates between Monohydroboration and Dihydroboration of Alkynes -- 4.3 Hydroboration Kinetics of Haloalkenes -- 4.4 Hydroboration Kinetics of Haloalkynes -- 4.5 Reduction Kinetics -- 4.6 Kinetics of Complex Formation -- 4.7 Kinetics of Protonolysis -- 5 Hydroboration -- 5.1 Hydroboration of Alkenes -- 5.1.1 Hydroboration of Acyclic Alkenes -- 5.1.2 Hydroboration of Cyclic Alkenes -- 5.1.3 Hydroboration of Chloro-, Acetate-, and Acetal-Functionalized Alkenes -- 5.1.4 Hydroboration of Allylsilanes -- 5.1.5 Hydroboration of Chiral Allyl Amines and Chiral Allyl Alcohols -- 5.1.6 Hydroboration of Alkenylheterocycles -- 5.1.7 Hydroboration of Enamines -- 5.1.8 Hydroboration of Heterocyclic Olefins -- 5.2 Hydroboration of Alkynes -- 5.2.1 Hydroboration of 1-Alkynes -- 5.2.2 Hydroboration of 1-Silyl-2-Alkyl-1-Alkynes -- 5.2.3 Hydroboration of 1-Halo-1-Alkynes -- 5.3 Hydroboration of Dienes -- 5.4 Hydroboration of Allenes -- 5.5 Hydroboration of Enynes and Diynes -- 6 Synthesis of Alcohols -- 6.1 Synthesis of Saturated Alcohols -- 6.2 Synthesis of Allylic Alcohols -- 6.3 Synthesis of Homoallylic Alcohols -- 6.4 Synthesis of Propargylic Alcohols -- 6.5 Synthesis of Homopropargylic Alcohols -- 6.6 Synthesis of Silyl Alcohols -- 6.6.1 Saturated Alcohols -- 6.6.2 Allylic Alcohols -- 6.6.3 Homoallylic Alcohols -- 6.6.4 Homopropargylic Alcohols -- 6.6.5 Diyne Alcohols -- 6.6.6 Endiyne Alcohols -- 6.6.7 Diendiyne Alcohols -- 6.6.8 Allenic Alcohols -- 6.6.9 Allenene Alcohols -- 6.6.10 Allenyne Alcohols -- 6.6.11 Allendienyne Alcohols -- 6.7 Synthesis of Heterocyclic Alcohols -- 6.8 Synthesis of Amino Alcohols -- 6.9 Asymmetric Synthesis of Alcohols -- 7 Synthesis of Aldehydes and Ketones -- 7.1 Synthesis of Aldehydes -- 7.2 Synthesis of Ketones -- 7.2.1 Synthesis of Saturated and Aromatic Ketones -- 7.2.2 Synthesis of Enones -- 7.2.3 Synthesis of, -Ynones -- 7.2.4 Synthesis of Dienones -- 7.2.5 Synthesis of Conjugated Enynones -- 7.2.6 Synthesis of -Ketosilanes -- 7.2.7 Synthesis of 1-Metallacyclohexan-4-ones -- 7.2.8 Synthesis of Chiral Ketones -- 8 Synthesis of Carboxylic Acids -- 8.1 Synthesis of Unsaturated Acids -- 8.2 Synthesis of -Amino Acids -- 9 Synthesis of Esters -- 9.1 Synthesis of Achiral Esters -- 9.2 Synthesis of Chiral Esters -- 9.3 Synthesis of (E)-, -Unsaturated Esters -- 9.4 Synthesis of -Amino Acid Esters -- 10 Synthesis of Nitriles -- 10.1 Synthesis of Achiral Nitriles -- 10.2 Synthesis of Chiral Nitriles -- 10.3 Synthesis of (E)-, -Unsaturated Nitriles -- 1.
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Electronic reproduction; Available via World Wide Web
Additional Edition:
ISBN 9783540490753
Additional Edition:
Erscheint auch als Druck-Ausgabe Dhillon, Ranjit S. Hydroboration and organic synthesis Berlin : Springer, 2007 ISBN 9783540490753
Additional Edition:
ISBN 3540490752
Language:
English
Subjects:
Chemistry/Pharmacy
Keywords:
Organische Synthese
;
Hydroborierung
;
Borabicyclononane
DOI:
10.1007/978-3-540-49076-0
URL:
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