30240-38-1Relevant academic research and scientific papers
Iodine-Promoted Semmler–Wolff Reactions: Step-Economic Access to meta-Substituted Primary Anilines via Aromatization
Wang, Shi-Ke,You, Xia,Zhao, Da-Yuan,Mou, Neng-Jie,Luo, Qun-Li
, p. 11757 - 11760 (2017/09/07)
An atom- and step-economic access to an array of unprotected meta-substituted primary anilines was disclosed using the Semmler–Wolff reaction, promoted by molecular iodine. Therein, noble metal catalysts and inert atmosphere are unnecessary while the forcing reaction conditions and the lengthy synthesis can be avoided. The synthetic utility of this approach is evident in the de novo syntheses of three bioactive molecules with good total yields.
Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines
Hong, Wan Pyo,Iosub, Andrei V.,Stahl, Shannon S.
supporting information, p. 13664 - 13667 (2013/10/01)
Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd0(PCy3)2, and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.
Cyclohexanone derivatives : Synthons for substituted quinolines
Padmavathi,Jagan Mohan Reddy,Rajagopala Sarma,Padmaja,Bhaskar Reddy
, p. 467 - 472 (2007/10/03)
Substituted quinolines 4, 5, and 9 were reported from o-allyl ethers of cyclohexanone derivatives by [2,3] sigmatropic rearrangement followed by cyclization. All the new compounds were characterized by IR and 1H NMR spectra.
