113947-86-7Relevant academic research and scientific papers
Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis
Fei, Jun,Wang, Zhen,Cai, Zheren,Sun, Hao,Cheng, Xu
, p. 4063 - 4068 (2016/01/25)
An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.
Arylcyclopropane Photochemistry. Substituent Effects on the Photochemical 1,3-Hydrogen Migration of 1,1-Dimethyl-2-phenylcyclopropane
Hixson, Stephen S.,Gallucci, Charles R.
, p. 2711 - 2713 (2007/10/02)
Irradiation of 1,1-dimethyl-2-arylcyclopropanes 1a-g (Ar = p-CF3C6H4 (1a), m-CF3C6H4 (1b), p-CH3C6H4 (1c), m-CH3C6H4 (1d), C6H5 (1e), m-OCH3C6H4 (1f), p-OCH3C6H4 (1g) gave in every case a 2-methyl-4-aryl-1-butene (2a-g) via a 1,3-hydrogen migration, accompanied by lesser amounts of a 3-methyl-1-aryl-2-butene (3a-g).Rearrangement is a singlet-state process.Rate constants for rearrangement were determined from reactant fluorescence lifetimes and product quantum yields.The rates for rearrangament of 1 to 2 were as follows:1a, 25*106s-1; 1b,15*106s-1; 1c, 7.9*106s-1; 1d, 6.1*106s-1; 1e, 2.3*106s-1; 1f, 1.9*106s-1; 1g, 0.87*106s-1.It isconcluded that the energetics of cyclopropane ring opening are important in the rate-determining step of the reaction.
