The Dewar Benzene Radical Cation and Its Ring-Opening Reaction

2006 ◽  
Vol 128 (24) ◽  
pp. 7828-7834 ◽  
Author(s):  
Thomas Bally ◽  
Stephan Matzinger ◽  
Pawel Bednarek
Keyword(s):  
Radical Cation ◽  
Ring Opening ◽  
Ring Opening Reaction

Ring-Opening Reaction of Cyclobutene Radical Cation: Effect of Solvent on Competing Pathways

1999 ◽  
Vol 103 (2) ◽  
pp. 217-219 ◽  
Author(s):  
Vincenzo Barone ◽  
Nadia Rega ◽  
Thomas Bally ◽  
G. Narahari Sastry
Keyword(s):  
Radical Cation ◽  
Ring Opening ◽  
Effect Of Solvent ◽  
Cation Effect ◽  
Ring Opening Reaction ◽  
Competing Pathways

Photochemical isomerization of cyclobutene radical cation to 1,3-butadiene radical cation. A "nonelectrocyclic" ring-opening reaction?

1989 ◽  
Vol 111 (20) ◽  
pp. 7909-7914 ◽  
Author(s):  
J. N. Aebischer ◽  
T. Bally ◽  
K. Roth ◽  
E. Haselbach ◽  
F. Gerson ◽  
...  
Keyword(s):  
Radical Cation ◽  
Ring Opening ◽  
Ring Opening Reaction ◽  
Photochemical Isomerization

On the Conrotatory Ring Opening of 3-Carbomethoxycyclobutene Vis-À-Vis 3-Carbomethoxy-1,2-Benzocyclobutene and the Predominant Inward Opening of 3-Dimethylaminocarbonyl-1,2-Benzocyclobutene

2018 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Maddali L N Rao
Keyword(s):  
Transition State ◽  
Ring Opening ◽  
Electron Process ◽  
Ring Opening Reaction ◽  
Stable Species ◽  
Electron Event

<p>The torquoselectivity of conrotatory ring opening of 3-carbomethoxycyclobutene is controlled by p<sub>C1C2</sub>→s*<sub>C3C4</sub> and s<sub>C3C4</sub>→p*<sub>CO</sub> interactions in the transition state in a 4-electron process as opposed to only s<sub>C3C4</sub>→p*<sub>CO</sub> interaction in an apparently 8-electron event in 3-carbomethoxy-1,2-benzocyclobutene. The ring opening of 3-carbomethoxy-1,2-benzocyclobutene is sufficiently endothermic. We therefore argue that the reverse ring closing reaction is faster than the forward ring opening reaction and, thus, it establishes an equilibrium between the two and subsequently allows formation of the more stable species <i>via</i> outward ring opening reaction. Application of this argument to 3-dimethylaminocarbonyl-1,2-benzocyclobutene explains the predominantly observed inward opening.</p>

scholarly journals Expanding Monomers as Anti-Shrinkage Additives

Polymers ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 806
Author(s):  
Philipp Marx ◽  
Frank Wiesbrock
Keyword(s):  
Ring Opening ◽  
Covalent Bond ◽  
Volumetric Shrinkage ◽  
Structure Property ◽  
Atomic Packing ◽  
Materials Properties ◽  
Volumetric Expansion ◽  
Structure Property Relationships ◽  
Ring Opening Reaction ◽  
Measuring Techniques

Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

Design and synthesis of 1,8-Naphthalimide Functionalized Benzothiadiazoles

2021 ◽  
Author(s):  
Rajneesh Misra ◽  
Yogjivan Rout
Keyword(s):  
Ring Opening ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Design And Synthesis ◽  
Cross Coupling Reaction ◽  
Ring Opening Reaction

A series of multi acceptor based push-pull derivatives BTD2–BTD5 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling reaction followed by [2+2] cycloaddition–electrocyclic ring-opening reaction in which benzothiadiazole (BTD, A1), naphthalimide...

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Sign in / Sign up

Export Citation Format

Share Document