Journal ArticleDOI
[2 + 2]‐Cycloreversions
Ernst Schaumann,Roger Ketcham +1 more
TLDR
In this article, it was shown that four-membered rings can be cleaved thermally, Photochemically, or catalytically into two π-bonded fragments.Abstract:
Four-membered rings can be cleaved thermally, Photochemically, or catalytically into two π bonded fragments. Theoretical calculations, kinetic studies, and investigations of stereo- and regioselectivity have been undertaken to clarify the question of whether the reaction involves one or two steps and to permit predictions on its course. [2 + 2]-Cycloreversions have been used to clarify the structure of four-membered rings, to prepare highly reactive π electron-systems and–in combination with a [2 + 2]-cycloaddition–to protect double bonds. The combination of a cycloaddition and-reversion can be used to convert a carbonyl group into an olefin. Starting with compounds containing annelated four-membered rings, compounds with two functional groups or large ring systems can be prepared. [2 + 2]-Cycloreversions have also been discussed in connection with storage of solar energy.read more
Citations
More filters
Journal ArticleDOI
Fluorination Effects on Indacenodithienothiophene Acceptor Packing and Electronic Structure, End-Group Redistribution, and Solar Cell Photovoltaic Response.
Thomas J. Aldrich,Micaela Matta,Weigang Zhu,Steven M. Swick,Charlotte L. Stern,George C. Schatz,Antonio Facchetti,Ferdinand S. Melkonyan,Tobin J. Marks +8 more
TL;DR: A heretofore unrecognized solution-phase redistribution process between the 2-(3-oxo-indan-1-ylidene)-malononitrile-derived end-groups (EGs) of IDTT-based NFAs is identified and mechanistically characterized, and the effects on PSC performance are assessed.
Journal ArticleDOI
Stress-Responsive Polymers Containing Cyclobutane Core Mechanophores: Reactivity and Mechanistic Insights
TL;DR: The development of a class of cyclobutane bearing bicyclo[4.2.0]octane mechanophores that hold promise as active functional groups in new classes of stress-responsive polymeric materials is reported.
Journal ArticleDOI
Direct Photochemical Cleavage of the Cyclobutane Ring in Bicyclo[4.2.0]octane on 185nm Irradiation in Solution
Waldemar Adam,Thomas Oppenländer +1 more
Journal ArticleDOI
The Paternò-Büchi reaction - a comprehensive review.
TL;DR: The photochemical reaction between an excited state of carbonyl compounds and an alkene to give the oxetane deriving from a cycloaddition reaction (the Paternò-Büchi reaction) is presented, and the possible application of this reaction in organic synthesis is discussed, comparing the photochemical approach with the other approaches used to synthesize theOxetane ring.
Journal ArticleDOI
Ab initio MC-SCF study of thermal and photochemical [2 + 2] cycloadditions
TL;DR: In this paper, the results of a study of few prototypical polar and non-polar cycloadditions are presented at a level of theory where biradical and zwitterionic mechanisms can be treated in a balanced way (CAS-SCF).
References
More filters
Book
The chemistry of heterocyclic compounds
TL;DR: In this article, it was shown that one of the most common types of known quantities of phenyl phenyl is phenyl oxide (POP) oxide, which is a phenyl-oxyoxy phenyl (PE)-oxyoxyphenyl) that can be obtained from phenyl compounds.
Book
Introduction to organic chemistry
TL;DR: The covalent bond and shapes of molecules are discussed in detail in this paper, where Amino acids and proteins are represented as nucleophilic aliphatic substitution, and the reaction of benzene and phenols.