6337-59-3Relevant articles and documents
Crosslinked Internal Alkyne-Based Stereo Elastomers: Polymers with Tunable Mechanical Properties
Hsu, Yen-Hao,Dove, Andrew P.,Becker, Matthew L.
, p. 4649 - 4657 (2021/05/29)
New methods to introduce and control polymer network crosslinking and improve mechanical properties of the resulting materials have been investigated extensively. Common methods to enhance the mechanical properties of elastomers include "vulcanization"by
Synthesis and Photodimerization of 2- And 2,3-Disubstituted Anthracenes: Influence of Steric Interactions and London Dispersion on Diastereoselectivity
Geiger, Thomas,Haupt, Anne,Maichle-M?ssmer, C?cilia,Schrenk, Claudio,Schnepf, Andreas,Bettinger, Holger F.
, p. 10120 - 10135 (2019/08/26)
There is increased evidence that the effect of bulky groups in organic, organometallic, and inorganic chemistry is not only repulsive but can be attractive because of London dispersion interactions. The influence of the size of primary alkyl substituents in 2- and 2,3-positions of anthracenes on the diastereoselectivity (anti vs syn dimer) of the [π4s + π4s] photoinduced dimerization is investigated. The synthesis of the anthracene derivatives was achieved by Suzuki-Miyaura reaction of 2,3-dibromoanthracene with alkylboronic acids as well as by reduction of anthraquinones that were obtained from 2,3-disubstituted 1,3-butadienes and naphthoquinone followed by dehydrogenation. The mixtures of dianthracene isomers were analyzed with respect to the anti/syn-ratio of the products by X-ray crystallography and nuclear Overhauser effect spectroscopy. While for the 2,3-dimethylanthracene the anti and syn isomers were formed in equal amounts, the anti dimers are the major products in all other cases. A linear correlation (R2 = 0.98) between the steric size (Charton parameter) and the isomeric ratio suggests that the selectivity is dominated by classical repulsive steric effects. An exception is the iso-butyl substituent that produces an increased amount of the syn isomer. It is suggested that this is due to an exalted effect of London dispersion interactions.
Twisted Cycloalkynes and Remote Activation of “Click” Reactivity
Harris, Trevor,Gomes, Gabriel dos Passos,Ayad, Suliman,Clark, Ronald J.,Lobodin, Vladislav V.,Tuscan, Megan,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 629 - 640 (2017/12/07)
The “twisted and bent” cyclodecyne structural motif, intertwined with dormant electronic effects, opens a conceptually powerful way to control “click” reactivity. The endocyclic heteroatoms of cyclodecynes provide dual electronic activation via hyperconju