61077-30-3Relevant academic research and scientific papers
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.
supporting information, 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.
Lone selectivity of the decatungstate-sensitized photooxidation of 1-substituted cycloalkenes
Lykakis, Ioannis N.,Orfanopoulos, Michael
, p. 2131 - 2134 (2007/10/03)
Decatungstate-sensitized oxidation of alkyl and phenyl substituted cycloalkenes in the presence of molecular oxygen shows a general preference for hydrogen abstraction on the congested side of the double bond.
Photochemical Reactions of Contact Charge-Transfer Pairs of 1-Arylcyclohexenes and Oxygen
Kojima, Masanobu,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 3331 - 3336 (2007/10/02)
Photoexcitation of contact charge-transfer (CCT) pairs of 1-arylcyclohexenes 1 (aryl: phenyl, 4-methylphenyl, and 4-methoxyphenyl) and oxygen in acetonitrile and benzene gave 1,2-epoxy-1-arylcyclohexanes 2 as major products together with 2-aryl-2-cyclohexen-1-ols and acetophenones 4.Similar irradiation of the CCT pairs in methanol/acetonitrile afforded mainly 2-aryl 2-cyclohexen-1-ones, and 4.The formation of these products can be explained by photoinduced electron transfer in the excited CCT pairs generating radical cations of 1 and superoxide anions.
