21592-62-1Relevant academic research and scientific papers
Regioselective formation of cyclic and allylic hydroperoxides
Stratakis,Orfanopoulos
, p. 425 - 430 (1993)
A regioselective photosensitized oxygenation is reported for the preparation of cyclic and allylic hydroperoxides.
Selective C-H Allylic Oxygenation of Cycloalkenes and Terpenoids Photosensitized by [Cu(Xantphos)(neoc)]BF4
Kallitsakis, Michael G.,Gioftsidou, Dimitra K.,Tzani, Marina A.,Angaridis, Panagiotis A.,Terzidis, Michael A.,Lykakis, Ioannis N.
, p. 13503 - 13513 (2021/09/13)
We present herein for the first time the use of the [Cu(Xantphos)(neoc)]BF4 as a photocatalyst for the selective C-H allylic oxygenation of cycloalkenes into the corresponding allylic hydroperoxides or alcohols in the presence of molecular oxygen. The proposed methodology affords the products at good yields and has also been applied successfully to several bioactive terpenoids, such as geraniol, linalool, β-citronellol, and phytol. A mechanistic study involving also kinetic isotope effects (KIEs) supports the proposed singlet oxygen-mediated reaction. On the basis of the high chemoselectivity and yields and the fast and clean reaction processes observed, the present catalytic system, [Cu(Xantphos)(neoc)]BF4, has also been applied to the synthesis, at a laboratory scale, of the cis-Rose oxide, a well-known perfumery ingredient used in rose and geranium perfumes.
Palladium-Catalyzed Asymmetric Allylic Fluoroalkylation/Trifluoromethylation
Trost, Barry M.,Gholami, Hadi,Zell, Daniel
supporting information, p. 11446 - 11451 (2019/08/20)
The first palladium-catalyzed asymmetric allylic trifluoromethylation is disclosed. The methodology evokes a fundamental principle by which the synergistic interplay of a leaving group and its subsequent activation of the nucleophilic trifluoromethyl grou
An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: Tapping into strain to access C 2-symmetric tricyclic rings
Singh, Kamaljeet,Trinh, Winston,Weaver, Jimmie D.
supporting information, p. 1854 - 1861 (2019/02/20)
A mild and operationally simple methodology is reported for the synthesis of cyclobutane rings imbedded within a C2-symmetric tricyclic framework. The method uses visible light and an iridium-based photocatalyst to drive the oft-stated "forbidden" thermal
Addition of hypobromous acid to 1-phenylcycloalkenes
Ceylan,Findik,Sahin,Kazaz
, p. 2299 - 2303 (2014/05/06)
Reaction of 1-phenylcyclooctene and 1-phenylcycloheptene with N-bromosuccinimide (NBS) in aqueous DMSO gives the corresponding 3-bromo-2-phenylcycloalkenes and 2-phenylcycloalk-2-enols in a ratio of 3: 1. Unlike them, 1-phenylcyclohexene gives a mixture of 3-bromo-2-phenylcyclohexene and 2-bromo-1-phenylcyclohexanol. The oxidation of allylic alcohols with pyridinium chlorochromate afforded the corresponding α,β-unsaturated ketones.
