3354-58-3Relevant academic research and scientific papers
Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
supporting information, (2020/05/18)
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation-Cyclization of Allylphenols
Triandafillidi, Ierasia,Sideri, Ioanna K.,Tzaras, Dimitrios Ioannis,Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 4254 - 4260 (2017/09/12)
A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o -allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H 2 O 2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o -allylphenols were cyclized in high yields..
PdI2-catalyzed regioselective cyclocarbonylation of 2-allyl phenols to dihydrocoumarins
Amzquita-Valencia, Manuel,Alper, Howard
supporting information, p. 5827 - 5829 (2015/01/08)
A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydrocoumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (L1) and 1,3,5,7-tetramethyl-6-tetradecyl-2,4,8-trioxa-6-phosphaadamantane (L2) were effective as ligands, affording good product selectivity in all cases.
Microwave-assisted zeolite catalyzed claisen rearrangement of allyl aryl ethers under solvent-free conditions
Deodhar, Deepak K.,Tipnis, Amol S.,Samant, Shriniwas D
experimental part, p. 1552 - 1555 (2011/02/23)
Claisen rearrangement of allyl aryl ethers has been studied extensively over various zeolites under microwave activation and solvent free conditions at 80°C. Hβ-zeolite is found to be an efficient catalyst for the rearrangement. The reaction gives ω-rearranged product selectively instead of expected further cyclized dihydrobenzofuran derivative.
Facile aromatic Claisen rearrangement catalysed by tin(IV) chloride
Sarkar, Debayan,Venkateswaran, Ramanathapuram V.
, p. 653 - 654 (2008/12/20)
Allyl aryl ethers undergo facile Claisen rearrangement under mild conditions catalysed by tin(IV) chloride. Georg Thieme Verlag Stuttgart.
Microwave-accelerated Claisen rearrangement in bicyclic imidazolium [b-3C-im][NTf2] ionic liquid
Lin, Yung-Lun,Cheng, Jen-Yen,Chu, Yen-Ho
, p. 10949 - 10957 (2008/02/13)
With microwaves, a chemically stable ionic liquid [b-3C-im][NTf2] recently developed in our laboratory was used as solvent and successfully applied to accelerate Claisen rearrangement reactions at high temperatures. In the presence of Lewis acid MgCl2, these thermal rearrangements could be achieved in similar reaction times but at lower temperature. For the microwaved reactions studied in this work, without scarifying isolated yields, the reaction times were significantly reduced from hours (by conventional heating) to ≤3 min. Our result also demonstrated that [b-3C-im][NTf2] ionic liquid was a useful solvent substitute and could be recycled multiple times for the studied rearrangement reaction at elevated temperatures.
Synthesis of aminomethylated derivatives of allylphenols and study of their antimicrobial characteristics in motor oil
Magerramov,Bairamov,Mekhtieva,Agaeva,Mamedova,Kulieva,Mamedov
, p. 665 - 668 (2008/02/14)
A series of nitrogen-containing compounds was synthesized by Mannich condensation of allylsubstituted derivatives of phenol and o-and p-cresols with formaldehyde and secondary amines. These compounds were studied as antimicrobial additives to motor oil (at a content of 1-2 wt %).
Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes
Walker, Edward R.,Leung, Shing Y.,Barrett, Anthony G.M.
, p. 6537 - 6540 (2007/10/03)
The isoquinolinone hemisphere of Sch 56036 has been prepared using a modified Pomeranz-Fritsch reaction and the synthesis of the phenanthrene core has been modelled via a Suzuki coupling and subsequent ring closing metathesis.
Rhodium- and iridium-catalyzed allylation of electron-rich arenes with allyl tosylate
Tsukada, Naofumi,Yagura, Yasushige,Sato, Tetsuo,Inoue, Yoshio
, p. 1431 - 1434 (2007/10/03)
The allylation of electron-rich arenes with allyl tosylate proceeded at 0°C in the presence of [Rh(nbd)(CH3CN)2]PF 6. Various oxygenated arenes were allylated with high para-selectivity in almost all cases. Especially in t
Water-Accelerated Claisen Rearrangements
Wipf, Peter,Rodriguez, Sonia
, p. 434 - 440 (2007/10/03)
Allyl aryl ethers undergo accelerated Claisen and [1,3] rearrangements in the presence of a mixture of trialkylalanes and water or aluminoxanes. The ratio of ortho-, meta-, and pora-Claisen products depends to a large extent on the presence of water and to a much lesser extent on the nature of the alane.
