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Stable Five-membered-ring Allenes With Second-row Elements Only: Not Allenes, But Zwitterions.

M. Christl, B. Engels
Published 2009 · Chemistry, Medicine

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A pyrazole derivative, considered as the stable five-membered cyclic allene 1 a by Dyker, Bertrand, et al., is reinterpreted to be a zwitterion 1 b. It is shown that the bonding characteristics typical for an allene are not possible for structure 1 a. Ar = 2,6-dimethylphenyl.
This paper references
10.1021/JA011227C
Computational assessment of the electronic structures of cyclohexa-1,2,4-triene, 1-oxacyclohexa-2,3,5-triene (3delta(2)-pyran), their benzo derivatives, and cyclohexa-1,2-diene. An experimental approach to 3delta(2)-pyran.
B. Engels (2002)
10.1002/1521-3765(20011015)7:20<4386::AID-CHEM4386>3.0.CO;2-S
The cyclization of parent and cyclic hexa-1,3-dien-5-ynes--a combined theoretical and experimental study.
M. Prall (2001)
10.1002/9783527619573.CH6
Cyclic Allenes Up to Seven‐Membered Rings
M. Christl (2008)
10.1016/S0040-4020(99)00013-7
Synthesis and structural studies of some [14]paracyclo-bis-(1,2)pyrazolium- and (1,3)imidazolium-phanes
P. Cabildo (1999)
10.1021/JP037010H
Comprehensive Model for the Electronic Structures of 1,2,4-Cyclohexatriene and Related Compounds
P. Musch (2003)
10.1002/anie.200801176
Synthesis and ligand properties of stable five-membered-ring allenes containing only second-row elements.
V. Lavallo (2008)
10.1021/JO060698K
Strain estimates for small-ring cyclic allenes and butatrienes.
Kimberly J. Daoust (2006)
10.1002/anie.200705615
Five-membered metallacyclic allenoids: synthesis and structure of remarkably stable strongly distorted cyclic allene derivatives.
Juri Ugolotti (2008)
10.1039/B611260A
β-Diiminato ligand (L) transformations in reactions of KL with PI3 and I2 [L = {N(C6H3Pri2-2,6)C(H)}2CPh]
P. Hitchcock (2007)
10.1002/CHEM.200305000
Computational Assessment of the Electronic Structure of 1-Azacyclohexa-2,3,5-triene (3 δ 2 -1 H -Pyridine) and Its Benzo Derivative (3 δ 2 -1 H -Quinoline) as well as Generation and Interception of 1-Methyl-3 δ 2 -1 H -quinoline
Jan C. Schöneboom (2003)
10.1002/ANGE.200705615
Metallacyclische Fünfring-Allenoide: Synthese und Struktur stabiler stark verzerrter cyclischer Allen-Derivate†
Juri Ugolotti (2008)
10.1107/S0108270191005103
Structure and conformation of a hetero-substituted cyclooctane
C. Foces-Foces (1991)
10.1039/B611260A
beta-Diiminato ligand (L) transformations in reactions of KL with PI3 and I2 [L = {N(C6H3Pr(i)2-2,6)C(H)}2CPh].
P. Hitchcock (2007)
10.1021/JA00092A069
Mechanism of the Reaction of Atomic Carbon with Pyrrole. Evidence for the Intermediacy of a Novel Dehydropyridinium Ylide
C. Emanuel (1994)
10.1021/JA9639168
THE CHEMISTRY OF THE N-METHYL-3-DEHYDROPYRIDINIUM YLID
Weitao Pan (1997)



This paper is referenced by
10.1002/ANGE.200905436
Funktionalisierte 4‐Aminochinoline durch Umlagerung von N‐heterocyclischen Carbenen des Pyrazols
A. Schmidt (2010)
10.1002/anie.200905436
Functionalized 4-aminoquinolines by rearrangement of pyrazole N-heterocyclic carbenes.
A. Schmidt (2010)
10.1021/acs.joc.5b01488
Dehydropericyclic Reactions: Symmetry-Controlled Routes to Strained Reactive Intermediates.
Sarah L. Skraba-Joiner (2015)
10.1002/anie.200901495
Tellurium(II)-centered dications from the pseudohalide "Te(OTf)2".
J. L. Dutton (2009)
10.1016/J.CCR.2016.07.008
Five-membered all-C- and hetero-metallacycloallenoids of group 4 metallocenes
Lisanne Becker (2017)
10.1002/chem.201904726
Dimerisation of Dipiperidinoacetylene: Convenient Access to Tetraamino‐1,3‐Cyclobutadiene and Tetraamino‐1,2‐Cyclobutadiene Metal Complexes
Ludwig Hackl (2019)
10.1039/d0dt00665c
Allene-derived gold and platinum complexes: synthesis and first applications in catalysis.
Hanna K Maliszewska (2020)
10.1002/chem.201000174
Carbodicarbenes and related divalent carbon(0) compounds.
S. Klein (2010)
10.1002/anie.200906697
Formation of cyclic allenes and cumulenes by cooperative addition of frustrated Lewis pairs to conjugated enynes and diynes.
Cornelia M. Mömming (2010)
10.1016/J.CHEMPHYS.2010.03.009
Mesomeric betaine chemistry in solution: Solvent effect on the structure and spectra of uracilyl–pyridinium betaine
A. Schmidt (2010)
10.1002/chem.200902737
Pyrazole-derived remote dicarbenes: versatile ligands for di- and tetranuclear complexes.
Y. Han (2010)
10.1007/128_2011_309
QM/MM investigations of organic chemistry oriented questions.
T. Schmidt (2014)
10.1021/ja904525a
Unusual bonding in trisilaallene and related heavy allenes.
M. Kira (2009)
10.1021/acs.joc.6b00561
Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines.
A. Schmidt (2016)
10.1002/ANGE.200906697
Cyclische Allene und Cumulene durch kooperative Addition frustrierter Lewis‐Paare an konjugierte Enine und Diine
Cornelia M. Mömming (2010)
10.1039/c002806a
An isolable dialkylsilylene and its derivatives. A step toward comprehension of heavy unsaturated bonds.
M. Kira (2010)
10.1002/JCCS.201600241
Carbodicarbenes or Bent Allenes
T. Wang (2017)
10.1016/J.CCR.2009.12.016
Five-membered metallacycloalkynes formed from group 4 metals and [n]cumulene (n = 3,5) ligands
Noriyuki Suzuki (2010)
10.1002/ANGE.201308609
Experimentelle Elektronendichteuntersuchung eines Silylons
Benedikt Niepoetter (2014)
10.1021/ja903396e
Exocyclic delocalization at the expense of aromaticity in 3,5-bis(pi-donor) substituted pyrazolium ions and corresponding cyclic bent allenes.
I. Fernández (2009)
10.1002/anie.201308609
Experimental charge density study of a silylone.
Benedikt Niepoetter (2014)
10.1002/CHIN.200917055
Stable Five‐Membered‐Ring Allenes with Second‐Row Elements Only: Not Allenes, but Zwitterions
Manfred Christl (2009)
10.1002/cctc.201701577
Carbodicarbenes and their Captodative Behavior in Catalysis
Shu-kai Liu (2018)
10.3987/COM-14-13082
SYNTHESES OF ACRIDINES AND QUINAZOLINE-2,4(1H,3H)-DITHIONES BY REARRANGEMENTS OF N-HETEROCYCLIC CARBENES OF INDAZOLE
A. Schmidt (2014)
10.1039/c7cc02525d
An unexpected rearrangement of pyrazolium halides based on N-N bond cleavage: synthesis of 1,2-dihydropyrimidines.
Q. Chen (2017)
10.1002/asia.201300887
Carbodicarbenes, carbon(0) derivatives, can dimerize.
David A Ruiz (2013)
10.1002/anie.201000165
Stable cyclic carbenes and related species beyond diaminocarbenes.
M. Melaimi (2010)
10.1021/jo302080c
Electronic structural trends in divalent carbon compounds.
H. Huynh (2013)
10.1007/430_2017_20
Synthesis and Structure of Carbodicarbenes and Their Application in Catalysis
Shu-kai Liu (2018)
10.1002/chem.200900249
On the electronic impact of abnormal C4-bonding in N-heterocyclic carbene complexes.
M. Heckenroth (2009)
10.1039/c0dt01037e
Pyrazolin-4-ylidenes: a new class of intriguing ligands.
Y. Han (2011)
10.1007/978-3-642-04722-0_5
Non-NHCs Stable Singlet Carbene Ligands
T. Kato (2010)
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