84174-10-7Relevant academic research and scientific papers
Contra-Thermodynamic, Photocatalytic E→Z Isomerization of Styrenyl Boron Species: Vectors to Facilitate Exploration of Two-Dimensional Chemical Space
Molloy, John J.,Metternich, Jan B.,Daniliuc, Constantin G.,Watson, Allan J. B.,Gilmour, Ryan
, p. 3168 - 3172 (2018/02/26)
Designing strategies to access stereodefined olefinic organoboron species is an important synthetic challenge. Despite significant advances, there is a striking paucity of routes to Z-α-substituted styrenyl organoborons. Herein, this strategic imbalance is redressed by exploiting the polarity of the C(sp2)?B bond to activate the neighboring π system, thus enabling a mild, traceless photocatalytic isomerization of readily accessible E-α-substituted styrenyl BPins to generate the corresponding Z-isomers with high fidelity. Preliminary validation of this contra-thermodynamic E→Z isomerization is demonstrated in a series of stereoretentive transformations to generate Z-configured trisubstituted alkenes, as well as in a concise synthesis of the anti-tumor agent Combretastatin A4.
A Synthesis of Conjugated Dienes from Aromatic, Five-membered Heterocycles
Wenkert, Ernest,Leftin, Michael H.,Michelotti, Enrique L.
, p. 617 - 618 (2007/10/02)
Reactions of furan, thiophene, selenophene, and tellurophene as well as 2-methyl and 2,5-dimethyl derivatives of the first two heterocycles with phenyl-, methyl-, and n-butyl-magnesium bromides in the presence of ligated nickel dichloride are shown to yield buta-1,3-dienes mostly with retention of configuration.
Reactions of Palladium(II) with Organic Compounds. Part 5. Effect of Reaction Conditions upon Products of Oxidation of α-Methylstyrene
Norman, Richard O. C.,Thomas, C. Barry,Watson, Grenville
, p. 1099 - 1104 (2007/10/02)
The effects upon product distribution of varying the temperature, time of reaction, and reagent concentrations have been investigated in the oxidation of α-methylstyrene by palladium(II) acetate.Two reaction pathways have been identified.A ?-allylic organopalladium compound decomposes slowly in a process catalysed by excess of the alkene to give 2-phenylprop-2-enyl acetate.The second reaction leads to competitive formation of enolic acetates and oxidative dimers but the organopalladium species involved has not been unambiguously identified.The addition of sodium acetate to the reaction, contrary to earlier reports, has only a marginal effect upon the distribution of products.
