57132-29-3Relevant academic research and scientific papers
Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols
Lübbesmeyer, Maximilian,Mackay, Emily G.,Raycroft, Mark A. R.,Elfert, Jonas,Pratt, Derek A.,Studer, Armido
, p. 2609 - 2616 (2020)
The Cα-Cβ bond in homoallylic alcohols can be activated under basic conditions, qualifying these nonstrained acyclic systems as radical allylation reagents. This reactivity is exemplified by photoinitiated (with visible light and/or
Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones
He, Yun,Agarwal, Piyush K.,Kiran, I. N. Chaithanya,Yu, Ruocheng,Cao, Bei,Zou, Cheng,Zhou, Xinghua,Xu, Huacheng,Xu, Biao,Zhu, Lei,Lan, Yu,Nicolaou
supporting information, p. 7696 - 7701 (2016/06/09)
A mild and practical method for the construction of heterocycles from N-substituted 2-oxazolones through cascade, BF3·Et2O/H2O-catalyzed reactions involving iminium ion generation and trapping by external or internal olefinic and aryl moieties is described. Mechanistic and computational studies revealed the strong protic acid HBF4as the initiating catalyst for these cascade reactions. Providing access to novel molecular diversity, these processes may facilitate chemical biology studies, drug discovery efforts and natural products synthesis.
Cyclopropene Photochemistry. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Bunce, Richard A.
, p. 3377 - 3396 (2007/10/02)
Four new cyclopropenes have been synthesized and their photochemistry has been investigated.Thus, 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene was found on direct photolysis to afford four photoproducts, the two major products of which derived from novel photochemistry. 2-Methylene-4-methyl-5,6-diphenyltetracyclo1,504,6>undeca-8,10-diene derived from cycloaddition of the excited cyclopropenyl ? bond to the C-1,C-2 ? bond of the phenyl of the 2-phenylallyl side chain.The quantum yield for this novel transformation was 0.023.A second photoproduct was 2-methyl-1,4,6-triphenyltricyclo2,6>hexane.This product results from a formal cycloaddition of the excited cyclopropenyl ? bond to the allyl double bond.A diradical mechanism is structurally equivalent.Formation of such a tricyclic 2,6> system is normally not found in direct irradiations.The quantum yield for this product was 0.088.Also formed was 3-methyl-1,2,5-triphenylbicyclohex-2-ene with an efficiency of 0.019.This product is understood as deriving either (i) from cyclopropene opening to a carbene which then adds to the allyl ? bond or (ii) from a bicyclic diradical arising from vinyl-vinyl bonding.The fourth photoproduct is 2-methyl-1,3-diphenyl-3-(2-phenylallyl)cyclopropene.The efficiency was 0.018.The bicyclic diradical above provides a common species leading to the last three products.Sensitization led only to the first two products: the tetracyclic diene (φ=0.26) and the tricyclo2,6>hexane (φ=0.15).Product structures were established by X-ray, degradation, independent synthesis, and spectral analysis.In addition, the photochemistry of cis- and trans-2,6-dimethyl-1,6-diphenylspirooct-1-ene was investigated.Stereoisomerization resulted from the singlet but not the triplet.Mechanisms for the above transformations are considered.Finally, corresponding thermal chemistry exhibited by the above compounds was investigated.
Chelate Control in the Rhodium-catalysed Homogeneous Hydrogenation of Chiral Allylic and Homoallylic Alcohols
Brown, John M.,Naik, Ramachandra G.
, p. 348 - 350 (2007/10/02)
Chelate bisphosphine rhodium complexes afford a high degree of stereoselection in the homogeneous hydrogenation of 3-phenylbut-3-en-2-ol and 4-phenylpent-4-en-2-ol, in opposite senses.
