53545-70-3Relevant academic research and scientific papers
Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids
Banerjee, Anamitro,Lee, Kwangjoo,Falvey, Daniel E.
, p. 12699 - 12710 (2007/10/03)
The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10- dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by- products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids.
Reactions of Copper(II) Halides with Aromatic Compounds. Part XII. Reactions of 9-Methyl-10-phenylanthracene, 1,4,9-Trimethylanthracene, 9,10-Dimethylanthracene and 1,5-Dichloro-9-methylanthracene in Methanol.
Mancilla, Jerson M.,Nonhebel, Derek C.,Scullion, Ian
, p. 1601 - 1619 (2007/10/02)
The title compounds react with copper(II) bromide in methanol to give the corresponding 9-methoxymethyl compounds. 1,4,9-Trimethylanthracene and 1,5-dichloro-9-methylanthracene also gave 1,2-di-(1,4-dimethyl-9-anthryl)ethane (6) and 1,5-dichloro-9,10-dimethoxy-9,10-dihydroanthracene (9) respectively.The formation of all these products can be interpreted in terms of initial electron transfer oxidation of the substituted anthracene to its radical cation, which either subsequently loses a proton to give the substituted 9-anthrylmethyl radical or undergoes solvent capture.
