112998-47-7Relevant academic research and scientific papers
Preparation of Hydroperoxides by N-Hydroxyphthalimide-Catalyzed Aerobic Oxidation of Alkylbenzenes and Hydroaromatic Compounds and Its Application
Fukuda, Osamu,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 809 - 813 (2001)
An efficient approach to phenols and aldehydes through the formation of hydroperoxides from alkylbenzenes was successfully achieved by aerobic oxidation using N-hydroxyphthalimide (NHPI) as a catalyst. The oxidation of various alkylbenzenes with dioxygen by NHPI followed by treatment with a Lewis acid or triphenylphosphine led to phenols or aldehydes, respectively, in good yields. For example, the aerobic oxidation of cumene in the presence of a catalytic amount of NHPI at 75°C and subsequent treatment with H2SO4 gave phenol in 77% yield. 1,4-Dihydroxybenzene (61%) and 4-isopropylphenol (33%) were obtained from 1,4-diisopropylbenzene. On the other hand, dibenzyl ether was converted into phenol or benzaldehyde upon treatment of the resulting hydroperoxide with InCl3 or PPh3, respectively.
PHOTOLACTONIZATION: A NOVEL SYNTHETIC ENTRY TO MACROLIDES
Quinkert, Gerhard,Billhardt, Uta-Maria,Jakob, Harald,Fischer, Gerd,Glenneberg, Juergen,et al.
, p. 771 - 821 (2007/10/02)
o-Quinol acetates, hydroxyalkylated at C(6), are easily accessible from simple phenols by Wessely acetoxylation (preferentially catalyzed by BF3).On UV irradiation (in the presence of an appropriate tertiary amine), they are smoothly converted to macrocyclic lactones.Subtle conditions have been elaborated to load to high overall yields, and the scope of the conversion of phenols to macrolides has been elucidated.
