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Junxia Li, Ronglin Pang, Zhifang Li, G. Lai, Xuqiong Xiao, T. Müller (2018)
Exceptionally Long C-C Single Bonds in Diamino-o-carborane as Induced by Negative Hyperconjugation.Angewandte Chemie, 58 5
L. Wallbaum, Tim Schulz, C. Bruhn, U. Siemeling (2019)
The reaction of a particularly electrophilic acyclic diaminocarbene with carbon monoxide: formation of β- and γ-lactamsZeitschrift für Naturforschung B, 74
M. Melaimi, Rodolphe Jazzar, Michèle Soleilhavoup, G. Bertrand (2017)
Cyclic (Alkyl)(amino)carbenes (CAACs): Recent Developments.Angewandte Chemie, 56 34
B. Alcaide, P. Almendros (2011)
Novel Aspects on the Preparation of Spirocyclic and Fused Unusual β-Lactams, 22
H. Chikashita, M. Miyazaki, K. Itoh (1984)
2-Phenylbenzothiazoline as a Reducing Agent in the Conjugate Reduction of α,β-Unsaturated Carbonyl CompoundsSynthesis, 1984
A. Napolitano, L. Panzella, Loredana Leone, M. d’Ischia (2013)
Red hair benzothiazines and benzothiazoles: mutation-inspired chemistry in the quest for functionality.Accounts of chemical research, 46 2
Xianqiang Huang, Nianxin Rong, Pengfei Li, G. Shen, Qiang Li, Nana Xin, Chuansheng Cui, Jichui Cui, Bingchuan Yang, Da-cheng Li, Changqiu Zhao, J. Dou, Bo Wang (2018)
AIBN-Promoted Synthesis of Bibenzo[ b][1,4]thiazines by the Condensation of 2,2'-Dithiodianiline with Methyl Aryl Ketones.Organic letters, 20 11
Sai Vummaleti, D. Nelson, A. Poater, Adrián Gómez‐Suárez, D. Cordes, Alexandra Slawin, S. Nolan, L. Cavallo (2018)
What can NMR spectroscopy of selenoureas and phosphinidenes teach us about the π-accepting abilities of N-heterocyclic carbenes?
Joan Vignolle, X. Cattoën, D. Bourissou (2009)
Stable noncyclic singlet carbenes.Chemical reviews, 109 8
Vincent Lavallo, Y. Canac, B. Donnadieu, W. Schoeller, G. Bertrand (2006)
CO fixation to stable acyclic and cyclic alkyl amino carbenes: stable amino ketenes with a small HOMO-LUMO gap.Angewandte Chemie, 45 21
A. Chakraborti, S. Rudrawar, Kirtikumar Jadhav, G. Kaur, S. Chankeshwara (2007)
“On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolinesGreen Chemistry, 9
Gerhard Wieland, G. Simchen (1985)
Synthese und Eigenschaften sterisch gehinderter tertiärer Amine und GuanidineEuropean Journal of Organic Chemistry, 1985
M. Barbazanges, L. Fensterbank (2012)
Chiral Acyclic Diaminocarbene Complexes: a New Opportunity for Gold Asymmetric CatalysisChemCatChem, 4
L. Slaughter (2014)
Catalysis with Acyclic Aminocarbene Ligands: Alternatives to NHCs with Distinct Steric and Electronic Properties
L. Slaughter (2012)
Acyclic Aminocarbenes in CatalysisACS Catalysis, 2
J. Palmer, G. Parkin (2013)
2-Seleno-1-alkylbenzimidazoles and their Diselenides: Synthesis and Structural Characterization of a 2-Seleno-1-methylbenzimidazole Complex of Mercury.Polyhedron, 52
D. Nelson, A. Collado, Simone Manzini, Sébastien Meiries, A. Slawin, D. Cordes, S. Nolan (2014)
Methoxy-Functionalized N-Heterocyclic CarbenesOrganometallics, 33
Kirsten Hogg, A. Trowbridge, Andrea Álvarez-Pérez, M. Gaunt (2017)
The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C–H bonds† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data and kinetic details. CCDC 1570476. For ESI and crystallographic data in CIF or otherChemical Science, 8
S. Bari, Aman Bhalla (2011)
Spirocyclic β-Lactams: Synthesis and Biological Evaluation of Novel Heterocycles, 22
Tim Schulz, Christian Färber, Michael Leibold, C. Bruhn, W. Baumann, D. Selent, Timo Porsch, M. Holthausen, U. Siemeling (2013)
Carbonylation of the simplest persistent diaminocarbene.Chemical communications, 49 61
Tim Schulz, D. Weismann, L. Wallbaum, Robin Guthardt, Charlotte Thie, Michael Leibold, C. Bruhn, U. Siemeling (2015)
New Stable and Persistent Acyclic Diaminocarbenes.Chemistry, 21 40
Benito Almendros (2002)
Recent Advances in the Stereocontrolled Synthesis of Bi- and Tricyclic-β-Lactams with Non-Classical StructureCurrent Organic Chemistry, 6
Libo Wang, Shuichi Nakamura, T. Toru (2004)
Highly enantioselective reaction of lithiated N-Boc-thiazolidine: a new chiral formyl anion equivalent.Organic & biomolecular chemistry, 2 15
Annika Liske, Kathrin Verlinden, Hannes Buhl, K. Schaper, C. Ganter (2013)
Determining the π-Acceptor Properties of N-Heterocyclic Carbenes by Measuring the 77Se NMR Chemical Shifts of Their Selenium AdductsOrganometallics, 32
A. Beckwith, D. Boate (1988)
Formation of fused tricyclic azetidinones and pyrrolidinones by intramolecular SH2 processesJournal of Organic Chemistry, 53
Y. Kumar, Prabhpreet Singh, G. Bhargava (2016)
Recent developments in the synthesis of condensed β-lactamsRSC Advances, 6
L. Wallbaum, D. Weismann, Dennis Löber, C. Bruhn, Pascal Prochnow, J. Bandow, U. Siemeling (2018)
Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO.Chemistry, 25 6
David Martin, Michèle Soleilhavoup, G. Bertrand (2011)
Stable singlet carbenes as mimics for transition metal centers.Chemical science, 2 3
H. Raubenheimer (2012)
Monomeric linear diaminocarbene complexes of gold(I) show merit in enantioselective catalysis.Angewandte Chemie, 51 21
A. Meijere, I. Kuchuk, V. Sokolov, T. Labahn, K. Rauch, M. Es-Sayed*, T. Krämer (2003)
Facile Preparation and Chemical Transformations of Spirocyclopropane‐Annelated HeterocyclesEuropean Journal of Organic Chemistry, 2003
C. Bebrone, P. Lassaux, Lionel Vercheval, J. Sohier, Adrien Jehaes, E. Sauvage, M. Galleni (2010)
Current Challenges in Antimicrobial ChemotherapyDrugs, 70
Jaime Cabrera‐Pardo, A. Trowbridge, M. Nappi, Kyohei Ozaki, M. Gaunt (2017)
Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C-H Bonds in Aliphatic Amines.Angewandte Chemie, 56 39
David Martin, Y. Canac, Vincent Lavallo, G. Bertrand (2014)
Comparative reactivity of different types of stable cyclic and acyclic mono- and diamino carbenes with simple organic substrates.Journal of the American Chemical Society, 136 13
M. McAllister, T. Tidwell (1994)
Comparative Cumulene Substituent Effects: Ketenes, Allenes, Diazomethanes, Diazirines, and Cyclopropenes by ab Initio Molecular Orbital CalculationsJournal of Organic Chemistry, 59
(2015)
Organometallic and Catalysis
M. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. Cascarano, L. Caro, C. Giacovazzo, G. Polidori, Dritan Siliqib, Riccardo Spagnac (2007)
IL MILIONE: a suite of computer programs for crystal structure solution of proteinsJournal of Applied Crystallography, 40
D. Buck, Doris Kunz (2015)
Triazine Annelated NHC Featuring Unprecedented Coordination VersatilityOrganometallics, 34
Kathrin Verlinden, Hannes Buhl, W. Frank, C. Ganter (2015)
Determining the Ligand Properties of N‐Heterocyclic Carbenes from 77Se NMR ParametersEuropean Journal of Inorganic Chemistry, 2015
Leyi Gong, M. McAllister, T. Tidwell (1991)
Substituent Effects on Ketene Structure and Stability: An ab initio StudyChemInform, 22
A. Meyers, P. Edwards, W. Rieker, T. Bailey (1984)
.alpha.-Amino carbanions via formamidines. Alkylation of pyrrolidines, piperidines, and related heterocyclesJournal of the American Chemical Society, 106
(2019)
Acta Crystallogr
D. Willcox, Ben Chappell, Kirsten Hogg, Jonás Calleja, Adam Smalley, M. Gaunt (2016)
A general catalytic β-C–H carbonylation of aliphatic amines to β-lactamsScience, 354
Michèle Soleilhavoup, G. Bertrand (2015)
Cyclic (alkyl)(amino)carbenes (CAACs): stable carbenes on the rise.Accounts of chemical research, 48 2
Catharina Goedecke, Michael Leibold, U. Siemeling, G. Frenking (2011)
When does carbonylation of carbenes yield ketenes? A theoretical study with implications for synthesis.Journal of the American Chemical Society, 133 10
A. McNally, B. Haffemayer, Beatrice Collins, M. Gaunt (2014)
Palladium-catalysed C–H activation of aliphatic amines to give strained nitrogen heterocyclesNature, 510
Yi Rong, Ahmed Al-Harbi, Benjamin Kriegel, G. Parkin (2013)
Structural characterization of 2-imidazolones: comparison with their heavier chalcogen counterparts.Inorganic chemistry, 52 12
B. Alcaide, P. Almendros (2004)
Beta-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest.Current medicinal chemistry, 11 14
Tim Schulz, Christian Färber, Michael Leibold, C. Bruhn, Pascal Prochnow, J. Bandow, T. Schneider, Timo Porsch, M. Holthausen, U. Siemeling (2014)
Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene.Chemical communications, 50 18
G. Frey, Vincent Lavallo, B. Donnadieu, W. Schoeller, G. Bertrand (2007)
Facile Splitting of Hydrogen and Ammonia by Nucleophilic Activation at a Single Carbon CenterScience, 316
Viney Gupta, Archna Sharma, S. Agrawal (2006)
Conformations, chemical reactivities and spectroscopic characteristics of some Di-substituted ketenes : An ab initio studyBulletin of The Korean Chemical Society, 27
S. Roy, K. Mondal, H. Roesky (2016)
Cyclic Alkyl(amino) Carbene Stabilized Complexes with Low Coordinate Metals of Enduring Nature.Accounts of chemical research, 49 3
K. Uneyama, H. Ohkura, J. Hao, H. Amii (2001)
A trial toward the synthesis of gamma-fluorinated beta-amino-alpha-thiohydroxyamino acid: a finding of desulfurizative C-C bond formation in thio-Wittig-type rearrangement of S-(N-aryl-trifluoroacetimidoyl)thioglycolates.The Journal of organic chemistry, 66 3
H. Duddeck (1995)
Selenium-77 nuclear magnetic resonance spectroscopyProgress in Nuclear Magnetic Resonance Spectroscopy, 27
U. Siemeling, Christian Färber, C. Bruhn, Michael Leibold, D. Selent, W. Baumann, Moritz Hopffgarten, Catharina Goedecke, G. Frenking (2010)
N-heterocyclic carbenes which readily add ammonia, carbon monoxide and other small molecules,Chemical Science, 1
Victoria Landry, M. Minoura, Ke-liang Pang, D. Buccella, B. Kelly, G. Parkin (2006)
Synthesis and structural characterization of 1-mesityl-1,3-dihydro-imidazole-2-selone and bis(1-mesitylimidazol-2-yl)diselenide: experimental evidence that the selone is more stable than the selenol tautomer.Journal of the American Chemical Society, 128 38
Beatriz Cordero, V. Gómez, Ana Platero‐Prats, M. Reves, J. Echeverría, E. Cremades, F. Barragán, S. Alvarez (2008)
Covalent radii revisited.Dalton transactions, 21
V. Boyarskiy, K. Luzyanin, V. Kukushkin (2012)
Acyclic diaminocarbenes (ADCs) as a promising alternative to N-heterocyclic carbenes (NHCs) in transition metal catalyzed organic transformationsCoordination Chemistry Reviews, 256
E. Anslyn, D. Dougherty (2005)
Modern Physical Organic Chemistry
M. Kinzhalov, V. Boyarskii (2015)
Structure of isocyanide palladium(II) complexes and their reactivity toward nitrogen nucleophilesRussian Journal of General Chemistry, 85
M. Gómez-Gallego, M. Mancheño, M. Sierra (2000)
Non-Classical Polycyclic β-LactamsTetrahedron, 56
Yamei Lin, Guo-ping Lu, Rongkang Wang, Wen-bin Yi (2016)
Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions.Organic letters, 18 24
H. Loghmani-Khouzani, Panteha Tamjidi, I. Mohammadpoor‐Baltork, Marzieh Yaeghoobi, N. Rahman, A. Khosropour, M. Moghadam, S. Tangestaninejad, Valiolah Mirkhani, M. Habibi, Ayana Kashima, Takayoshi Suzuki (2014)
Efficient and Eco‐friendly Syntheses of 1,5‐Benzothiazepines and 1,5‐Benzodiazepines Catalyzed by [Hmim][NO3] under Mild ConditionsJournal of Heterocyclic Chemistry, 51
Ursula Paul, U. Radius (2017)
What Wanzlick Did Not Dare To Dream: Cyclic (Alkyl)(amino)carbenes (cAACs) as New Key Players in Transition‐Metal ChemistryEuropean Journal of Inorganic Chemistry, 2017
V. Boyarskiy, N. Bokach, K. Luzyanin, V. Kukushkin (2015)
Metal-mediated and metal-catalyzed reactions of isocyanides.Chemical reviews, 115 7
Libo Wang, Shuichi Nakamura, Yuji Ito, T. Toru (2004)
Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalentsTetrahedron-asymmetry, 15
M. Hirano, K. Osakada, H. Nohira, A. Miyashita (2002)
Crystal and solution structures of photochromic spirobenzothiopyran. First full characterization of the meta-stable colored species.The Journal of organic chemistry, 67 2
AbstractThe reaction of [iPr2N=CHCl]Cl with 2-phenylbenzthiazolidine (Ph-BtzH) and subsequent anion metathesis afforded the formamidinium salt [(Ph-Btz)CH(NiPr2)][PF6] ([1aH][PF6]). The reaction of [1aH][PF6] with (Me3Si)2NNa in the presence of grey selenium furnished the selenourea derivative 1aSe as trapping product of the acyclic diaminocarbene 1a. In the absence of selenium, a 2H-1,4-benzothiazine derivative (2) was obtained, which is an isomer of 1a, whose formation is plausibly initiated by deprotonation of [1aH]+ not at the cationic N2CH unit, but at the neighbouring PhCH position. CO was ineffective as trapping reagent for 1a. [1aH][PF6], 1aSe and 2 have been structurally characterised by X-ray diffraction.
Zeitschrift für Naturforschung B – de Gruyter
Published: Apr 24, 2019
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