31952-17-7Relevant academic research and scientific papers
Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
He, Jia,Jia, Zizi,Tan, Hongcheng,Luo, Xiaohua,Qiu, Dachuan,Shi, Jiarong,Xu, Hai,Li, Yang
, p. 18513 - 18518 (2019/11/19)
A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.
Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: Remarkable trans-addition of organoboronic reagents
Tsukamoto, Hirokazu,Ueno, Tatsuhiko,Kondo, Yoshinori
, p. 1406 - 1407 (2007/10/03)
Palladium/monophosphine complexes catalyze trans-selective arylative, alkenylative, and alkylative cyclization reactions of alkynals and alkynones with organoboronic reagents. These reactions afford six-membered allylic alcohols with endo-tri- or tetrasub
Transmission of Substituent Effects through Unsaturated Systems. Part 6. Kinetics of Reduction of β-Substituted α, β-Unsaturated Ketones with Sodium Borohydride
Geribaldi, Serge,Decouzon, Michele,Boyer, Bernard,Moreau, Claude
, p. 1327 - 1330 (2007/10/02)
The rate constants for addition of sodium borohydride to 3-substituted 5,5-dimethylcyclohex-2-enones (1), para-substituted 3-phenylcyclohexenones (2), and para-substituted acetophenones (3) have been determined in an alkaline solution (NaOH, 0.025 mol l-1) of water-dioxane (1:1 v/v) at 298 K.The conjugated cyclohexenone systems (1) and (2) undergo exclusive 1,2-reduction in these conditions to produce the corresponding allylic alcohols.The regioselectivity of reduction is discussed.The linear free energy relationships obtained between the rate constants and ?p or ?p+ confirm that these 3-substituted cyclohexenone structures are good models for the investigation of the substituent effects on the reactivity of ethylenic systems.Comparison of reaction constants for the three series leads to the conclusion that, as for borohydride reductions of acetophenone, the cyclohexenone reduction must have a late transition state in the final quarter of the reaction co-ordinate.
