84107-47-1

Upstream product

• 25679-28-1 cis-Anethole 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 104-46-1 anethole 
• 764-42-1 1,2-Dicyanoethylene 
• 1073-67-2 4-vinylbenzyl chloride 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 100-42-5 styrene 
• 19043-23-3 syn-(1α,2β,3β,4β)-1,2-bis(4-methoxyphenyl)-3,4-dimethylcyclobutane 

Downstream Products

• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 

Relevant academic research and scientific papers

Photoinduced electron transfer reactions of aryl olefins. 2. Cis-trans isomerization and cycloadduct formation in anethole-fumaronitrile systems in polar solvents

In acetonitrile, the photoreactions of cis-anethole, cA, or trans-anethole, tA, with fumarodinitrile, FN, lead to isomerization of both substrate and quencher and to mixed [2 + 2] cycloaddition. By NMR analysis and by NOE measurements it was shown that th

Host-Guest-Induced Electron Transfer Triggers Radical-Cation Catalysis

Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an "electron hole" will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species.

Benign catalysis with iron: Facile assembly of cyclobutanes and cyclohexenes: Via intermolecular radical cation cycloadditions

We describe novel and facile iron-catalyzed crossed intermolecular radical cation cycloadditions of styrenes. This catalysis features high efficiency, atom economy, stereospecificity, scalability and very mild reaction conditions. Thus, these reactions re

Investigating radical cation chain processes in the electrocatalytic Diels-Alder reaction

Single electron transfer (SET)-triggered radical ion-based reactions have proven to be powerful options in synthetic organic chemistry. Although unique chain processes have been proposed in various photo- and electrochemical radical ion-based transformati

Electronically Mismatched Cycloaddition Reactions via First-Row Transition Metal, Iron(III)-Polypyridyl Complex

The iron(III)-polypyridyl complex and its derivatives showed sufficient oxidizing potential to act as a one-electron oxidant, producing radical cations from olefins and promoting the efficient radical cation [2 + 2] and [2 + 4] cycloaddition reactions. Subsequent chain propagation afforded trisubstituted cyclobutane or cyclohexene derivatives, and this facile route enables the replacement of rare metals with sustainable, green, and inexpensive iron in radical cation cycloadditions.

Visible-Light-Irradiated Graphitic Carbon Nitride Photocatalyzed Diels–Alder Reactions with Dioxygen as Sustainable Mediator for Photoinduced Electrons

Photocatalytic Diels–Alder (D–A) reactions with electron rich olefins are realized by graphitic carbon nitride (g-C3N4) under visible-light irradiation and aerobic conditions. This heterogeneous photoredox reaction system is highly e

Development of solvent-driven iron-catalyzed reactions

The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3～5 mol% of Fe(ClO4 )3 ?Al2 O3 or Fe(BF4 )2 ?6H2 O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6 ] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3～5 mol% of Fe(ClO4 )2 ?Al2 O3 or Fe(BF4 )2 ?6H2 O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or α-aryl-β-silylalcohol. In particular, the reaction of chiral α-aryl-β-silylalcohol with indole using Fe(ClO4 )3 ?nH2 O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4 )2 /Pybox. We further demonstrated that Fe(ClO4 )3 ?Al2 O3 -catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.

Synthesis of cyclobutane lignans via an organic single electron oxidant-electron relay system

A direct method to synthesize lignan cyclobutanes and analogs via photoinduced electron transfer is presented. A variety of oxygenated alkenes are employed to furnish terminal or substituted cyclobutane adducts with complete regiocontrol, yielding cycload

Anethole isomerization and dimerization induced by acid sites or UV irradiation

The formation of cis-anethole and various dimers as a result of the exposure of trans-anethole to microporous solid acids (dealuminated HY zeolites), or UV-Vis irradiation was established by means of high resolution gas chromatography coupled to mass spectrometry. 3,4-bis-(4-Methoxyphenyl)-(E)-hex- 2-ene was the most abundant compound among eight different methoxyphenyl- disubstituted hexenes produced by electrophilic addition and elimination reactions induced by HY zeolites. (1a,2a,3b,4b)-1,2-bis(4-Methoxyphenyl)-3,4- dimethylcyclobutane was the principal component in the mixture of 5 methoxyphenyl-disubstituted cyclobutanes found, together with cis-anethole, after UV-Vis irradiation of a trans-anethole solution in toluene.

[2+2]-cycloaddition reaction of styrene derivatives using an Fe(III) salt catalyst

Iron(III) perchlorate catalyzed cyclodimerization of trans-anethole gave trans,anti,trans-cyclobutane stereospecifically in good yield. Alumina supported iron(III) perchlorate was an especially efficient one-electron oxidation reagent.