74663-59-5Relevant academic research and scientific papers
Functionalized Allyl Aryl Ether Synthesis from Benzoic Acids Using a Dearomatization and Decarboxylative Allylation Approach
Hsieh, Cheng-En,Jiang, Yu-Min,Chou, Chih-Ming
supporting information, p. 653 - 665 (2019/01/24)
A strategy toward the preparation of substituted allyl aryl ethers from benzoic acids via a dearomatization and decarboxylative allylation (DcA) reaction is presented. The benzoic acids undergo a dearomatization to give alkylated 2,5-cyclohexadienyl ketoesters which are subjected to a palladium-catalyzed DcA reaction, providing a variety of functionalized allyl aryl ethers. In addition, the combination of a resonance stabilized DcA reaction with a Claisen rearrangement for the synthesis of multisubstituted phenols and applying to dihydroplicatin B derivative synthesis is also presented.
Enantioselective synthesis of benzofurans and benzoxazines via an olefin cross-metathesis-intramolecular oxo-Michael reaction
Zhang, Jun-Wei,Cai, Quan,Gu, Qing,Shi, Xiao-Xin,You, Shu-Li
, p. 7750 - 7752 (2013/09/02)
Chiral phosphoric acid and Hoveyda-Grubbs II were found to catalyze an olefin cross-metathesis-intramolecular oxo-Michael cascade reaction of the ortho-allylphenols and enones to provide a variety of benzofuran and benzoxazine derivatives in moderate to good yields and enantioselectivity.
Alumina-Catalyzed Reactions of Hydroxyarenes and Hydroaromatic Ketones. 9. Reaction of Phenol with 1-Propanol
Klemm, LeRoy H.,Taylor, Dennis R.
, p. 4320 - 4326 (2007/10/02)
At 250-350 deg C in the presence of alumina, phenol (1) reacts with excess 1-propanol to give mainly (>90percent) C-alkylation to form mono- to penta-n-propylphenols plus some O-alkylations to form n-propyl aryl ethers. The principal component of the product mixture from 1 is 2,6-di-n-propylphenol (26-50 mol percent yield). With 4-n-propylphenol as substrate (instead of 1), tri-, tetra-, and penta-n-propylphenols are formed in 48-79percent combined yield. On the average, only 3percent of the total C3H7 groups in the product mixture are isopropyl ones. Deoxygenation is not observed. It is proposed that the principal products result from an SN2-type reaction mechanism which involves nucleophilic attack (variously by C-2, C-4, C-6, or O) of an adsorbed ambident phenoxide ion onto C-1 of an adsorbed n-propoxide group. n-Propylation at C-3 and C-5 of the phenol ring results from surface-catalyzed dienone-phenol rearrangement.Isopropylation may occur via a side reaction of SN1 type.
