14562-09-5Relevant articles and documents
Regio- and diastereoselective stepwise [8 + 3]-cycloaddition reaction between tropone derivatives and donor-acceptor cyclopropanes
Rivero, Alexandra R.,Fernandez, Israel,Sierra, Miguel Angel
, p. 4928 - 4931 (2013)
A novel SnCl4-catalyzed [8 + 3]-cycloaddition reaction between tropone derivatives and donor-acceptor aminocyclopropanes is described. The process leads to the formation of amino-substituted tetrahydrocyclohepta[b] pyrans with complete regio- and diastereoselectivity. Density functional theory calculations suggest that the cycloaddition occurs stepwise through an aromatic zwitterionic intermediate.
The Effect of Base and Nucleophile on the Nucleophilic Substitution of Methoxytropone Derivatives: An Easy Access to 4- And 5-Substituted Multifunctional Azulenes
Kumar, Neha R.,Agrawal, Abhijeet R.,Choudhury, Aditya,Zade, Sanjio S.
, p. 9029 - 9041 (2020/08/14)
The nucleophilic substitution on 3-substituted 2-methoxytropones to form azulenes is dependent on the nucleophile and base employed. With bulkier nucleophiles (ethyl/methyl cyanoacetate), the reaction proceeds with the abnormal nucleophilic substitution i
Abnormal Nucleophilic Substitution on Methoxytropone Derivatives: Steric Strategy to Synthesize 5-Substituted Azulenes
Kumar, Neha Rani,Agrawal, Abhijeet R.,Zade, Sanjio S.
, p. 14064 - 14071 (2019/11/03)
Azulene is a non-alternant non-benzenoid aromatic system, and in turn, it possesses unusual photophysical properties. Azulene-based conjugated systems have received increasing interest in recent years as optoelectronic materials. Despite the routes availa
Innermolecular reactions of fluorophenylcarbene inside a hemicarcerand
Lu, Zhifeng,Moss, Robert A.,Sauers, Ronald R.,Warmuth, Ralf
supporting information; experimental part, p. 3866 - 3869 (2009/12/05)
Photolysis of fluorophenyldiazirine, incarcerated in hemicarcerand 2, affords fluorophenylcarbene, which attacks an aryl unit of the host, leading (after rearrangement) to a fluoromethoxy/phenyltropone derivative of the hemicarcerand. The incarcerated car
Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
Seganish, W. Michael,DeShong, Philip
, p. 1137 - 1143 (2007/10/03)
Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
Synthesis of 5-Methoxy- and 5-(Dialkylamino)bicyclohept-2-en-6-one Derivatives by cine Substitution with Methoxide Anions and Dialkylamines
Butenschoen, Holger
, p. 137 - 144 (2007/10/02)
exo-7-Chloro-endo-7-phenylbicyclohept-2-en-6-one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5-methoxy or 5-dialkylamino derivatives 13, 14, 16-19 in high yield.While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield.Hydrochlorides 20/21 lose amine at 110 deg C to form 2-phenyltropone (22).Thermolysis of diethylamino derivative 24 at 170 deg C (temperature determined by DSC) results in the formation of the dienoaminone 25. - Key Words: Bicyclohept-2-en-6-one, cine substitution / DSC
5-Substituted Bicyclohept-2-en-6-ones: Synthesis and Ring-opening Reactions
Butenschoen, Holger
, p. 483 - 484 (2007/10/02)
5-Methoxy- and 5-dialkylamino-bicyclohept-2-en-6-one derivatives 2 and 3 are formed in high yield by cine substitution at the fused exo-chlorocyclobutanone 1, subsequent reactions yielding 2-phenyltropone 6 and a cycloheptadienone enamine 8.
NEW ROUTES TO SUBSTITUTED TROPONES
Barbosa, Luiz-Claudio Almeida,Mann, John,Wilde, Philip D.,Finch, Mark W.
, p. 4619 - 4626 (2007/10/02)
We descibe the synthesis of various mono- and di-substituted tropones from 8-oxabicyclooctenones, and also two novel cleavage reactions of these oxabicycles.
The reaction of tropone and tropilidene derivatives with palladium acetate in benzene
Saito, Katsuhiro
, p. 265 - 268 (2007/10/02)
Reaction of tropone or tropilidene derivatives with palladium acetate in benzene gave the following results.Tropone yielded 2-phenyltropone and 2,7-diphenyltropone. 2-Methoxytropone gave 2-methoxy-7-phenyltropone.Tropilidene yielded 1-phenyltropilidene but 7-methoxytropilidene gave tropone.
New Functionalized Cycloheptatrienes via Tropone ?-Adducts
Cavazza, Marino,Morganti, Gioia,Guerriero, Antonio,Pietra, Francesco
, p. 199 - 202 (2007/10/02)
We report that, on treatment with phenyl-lithium, followed by triethyloxonium tetrafluoroborate in diethyl ether at -78 deg C, (i) 2-chloro- and 2-bromo-tropone give the corresponding 1-ethoxy-2-halogeno-7-phenylcycloheptatriene; (ii) 2-fluorotropone gove
