Beiträge zur Chemie dea Bors. XX Zur Kenntnis von Alkyl‐bis(dimethylamino)‐boranen

Nöth, Heinrich; Fritz, P.

doi:10.1002/zaac.19633220509

Cited by 76 publications

(8 citation statements)

References 14 publications

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“…Nöth and Fritz considered the possible role of n -stabilized aminoborenium ions in the protonation of bis(dialkylamino)boranes during the 1960’s, 28 but convincing evidence was not obtained until well-behaved substrates were encountered in the 1,3-diazaborolidine series (Scheme 1). 29 Thus, protonation of 26 with triflic acid generated the amine-stabilized cation 27 in solution ( 11 B δ = 25.8 ppm).…”

Section: History Of Borenium Ions: Often Considered Seldom Confirmedmentioning

confidence: 99%

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

2012

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CONTENTS 1. Introduction 4246 2. History of Borenium Ions: Often Considered, Seldom Confirmed 4247 2.1. Suspected Intermediates in B−N Protonation 4247 2.2. Hypothetical Isomers of Cl 3 B•NHMe 2 4247 2.3. The First Observable Borenium Salt 4247 2.4. Nucleophilic Substitution of X 3 B•NR 3 and Py•BF 2 X 4248 2.5. Aminoborenium Ions, Stabilization by n-Delocalization 4249 3. Recent Developments in the Generation of Observable Borenium Intermediates 4249 3.1. Electrophilic Activation by Protonation or by Lewis Acid Catalysis 4249 3.2. Halide Abstraction by a Halophile 4250 3.3. The Borinium−Borenium Interface: Gas-Phase Oxyborenium Ions 4251 3.4. Borenium Salt Generation by Hydride Abstraction 4251 3 . 4 . 1 . H y d r i d e A b s t r a c t i o n b y T r i s -(pentafluorophenyl)borane 4251 3.4.2. Hydride Abstracton by Trityl Salts 4252 3.4.3. Hydride-Bridged Borenium Salt Dimers 4252 3.5. Borenium Ion Generation by Nucleophilic Addition−Heterolysis 4253 4. Borenium Lewis Acidity vs Structure 4254 4.1. Experimental Evaluation of Lewis Acidity 4254 4.2. Computational Evaluation of Borenium Lewis Acidity 4255 5. Borenium Ions and Stereogenic Boron 4257 5.1. Racemization by Heterolysis 4257 5.2. Asymmetric Memory at Stereogenic Boron 4257 5.3. Chiral Salicylaldimine Boronate Complexes 4258 6. Enantioselective Catalysis and Chiral Borenium Ions 4259 6.1. The Dual Function of Oxazaborolidines in the CBS Reduction 4260 6.2. The Role of Borenium Species in Diels−Alder Catalysis 4261 6.3. Reactivity and Scope of Oxazaborolidine-Derived Diels−Alder Catalysts 4263 6.4. Miscellaneous Uses of Chiral Borenium Lewis Acid Catalysts 4265 7. Miscellaneous Applications of Borenium Lewis Acids 4266 7.1. B−O Activation 4266 7.2. Lewis Acidity and π-Conjugated Borenium Analogues 4267 7.3. π-Conjugated Borenium Analogues as Selective Anion Sensors 4268 7.4. Tricoordinate Boron in Structures Containing Metal Cations 4269 8. Borenium Reagents for C−B Bond Formation 4269 8.1. Borenium Ion Equivalents 4269 8.2. Do Borenium Ions Participate in Hydroboration Chemistry? 4270 8.3. Borenium Equivalents in Electrophilic Aromatic Borylation 4271 8.3.1. Intramolecular Borylation 4271 8.3.2. Intermolecular Borylation 4272 8.3.3. Recent Developments in Muetterties Borylation (BX3 plus Proton Scavenger) 4275 9. Extension of Borenium Chemistry to Neighboring Fields and Unusual Environments 4276 9.1. N-Heterocyclic Carbenes as Stabilizing Ligands for Borenium Salts 4276 9.2. Miscellaneous Related Topics Involving BH Species 4277 10. Summary 4278 Author Information 4279 Corresponding Author 4279 Notes 4279 Biographies 4279 Acknowledgments 4279 References 4279

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Section: History Of Borenium Ions: Often Considered Seldom Confirmedmentioning

confidence: 99%

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

2012

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“…Brought to you by | MIT Libraries Authenticated Download Date | 5/10/18 4:08 AM [8] and bis(dimethylamino)phenylborane [9] were prepared by the indicated literature procedures. Elemental analyses were performed by the Schwarzkopf Microanalytical Laboratory, Woodside, NY.…”

Section: Methodsmentioning

confidence: 99%

Preparation and Characterization of Some Isoelectronic Boron-Nitrogen Analogs of Substituted Uracil [1]

Bielawski

Niedenzu

Stewart

1985

Zeitschrift Für Naturforschung B

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“…One relevant example employing [(CH 3 ) 2 N](C 6 H<)BOB(C 6 H)[N(CH 3 ) 2 J (1c) has already been described. 4 The present study reports the preparation, characterization, and representative reactions of some [4][5][6][7][8][9][10][11][12][13][14][15][16] as the starting material. However, distillation under vacuum gave only a product of bp 125 'C (1 Torr) which was contaminated by ca.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Reactions of Di(aminoboryl) Oxides

Komorowska¹,

Niedenzu²,

Weber³

1989

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Beiträge zur Chemie dea Bors. XX Zur Kenntnis von Alkyl‐bis(dimethylamino)‐boranen

Abstract: Alkyl‐bis(dimethylamino)((dimethylamino))borane erhält man bei der Dimethylaminolyse von Alkylbordichloriden oder bei der Alkylierung von Bis(dimethylamino)‐chloroboran mit Alkyl‐Lithium. Ihr Verhalten gegenüber den Halogenwasserstoffen HCl, HBr und HJ wurde untersucht.

Cited by 76 publications

References 14 publications

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective

Preparation and Characterization of Some Isoelectronic Boron-Nitrogen Analogs of Substituted Uracil [1]

Preparation and Reactions of Di(aminoboryl) Oxides

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