- Studies related to the total synthesis of the sesquiterpene core of the pyrrolobenzoxazine natural products CJ-12662 and CJ-12663
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A highly effective procedure is reported to synthesize a substituted bicyclo[4.2.0]octenol derivative by regioselective cycloaddition of phenyl-1-propynyl sulfide with cyclohexenone followed by selective reduction of the ketone group and reductive elimina
- Commandeur, Ma?gorzata,Commandeur, Claude,Paolis, Michael De,Edmunds, Andrew J.F.,Maienfisch, Peter,Ghosez, Léon
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- Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides
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Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides on heating with solid potassium hydroxide afforded the corresponding 1-(organylsulfanyl)propynes in moderate to high yields and minor isomeric allene derivatives, organylsulfanylpropadienes.
- Rozentsveig,Nikonova,Levanova,Korchevin
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p. 1264 - 1266
(2016/10/26)
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- Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
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Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.
- Racine, Sophie,Hegedüs, Bence,Scopelliti, Rosario,Waser, Jér?me
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supporting information
p. 11997 - 12001
(2016/08/16)
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- Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- Or β- π-Addition?
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The alkynylation of thiols with EthynylBenziodoXolone (EBX) reagents is a fast and chemoselective method for the synthesis of thioalkynes. Combined experimental and computational studies are reported, which led to the identification of a new mechanism for
- Wodrich, Matthew D.,Caramenti, Paola,Waser, Jerome
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- Mechanism and stereochemistry of domino reaction of 2,3-dichloroprop-1-ene with diphenyl dichalcogenides in the system hydrazine hydrate - KOH
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A new scheme of the domino reactions of diphenyl dichalcogenides with 2,3-dichloroprop-1-ene in the system hydrazine hydrate - KOH was suggested, which included nucleophilic substitution of the allylic chlorine atom in dichloropropene, dehydrochlorination of the product obtained with the formation of an allene derivative, addition of a nucleophile to the allene system, allene-acetylene rearrangement, addition of a nucleophile to the triple bond with the formation of a Z-adduct, isomerization of a 2,3-dichalcogenide product to Z-1,2-dichalcogenylprop-1-enes, and isomerization of Z-adducts to E-isomers. The most plausible mechanisms of individual steps, involving carbanions stabilized by the α-chalcogen atom, were considered.
- Levanova,Vakhrina,Grabel'Nykh,Rozentsveig,Russavskaya,Albanov,Korchevin
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p. 1722 - 1727
(2015/05/20)
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- Domino reaction of 2,3-dichloroprop-1-ene with diphenyl disulfide in the system hydrazine hydrate-potassium hydroxide
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2,3-Dichloroprop-1-ene reacted with diphenyl disulfide in the system hydrazine hydrate-potassium hydroxide at 30-35 C to give three products: 2-chloro-3-phenylsulfanylprop-1-ene, 1-phenylsulfanylpropadiene, and 1-phenylsulfanylprop-1-yne. Variation of tem
- Levanova,Grabel'Nykh,Elaev,Russavskaya,Klyba,Albanov,Tarasova,Korchevin
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p. 1341 - 1344
(2013/09/23)
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- Prototropic rearrangement of 2-propynyl(methyl)amino, 2-propynyloxy, and 2-propynylsulfanyl derivatives of hetarenes under conditions of phase-transfer catalysis: Mechanism and limitations
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2-Propynyl derivatives of N-methylaniline, phenol, benzenethiol, 2-pyridinethiol, 2-pyrimidinethiol, and 1,3-benzoxazole-2-thiol were synthesized. Under conditions of phase-transfer catalysis, phenyl 2-propynyl sulfide is converted into allenyl phenyl sul
- Rubina,Fleisher,Abele,Popelis,Lukevits
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p. 963 - 967
(2007/10/03)
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- Rearrangements of 2-Phenylthioethanols with Alkenyl, Alkynyl, Ester, and Other Functionalised Alkyl Substituents at the Migration Origin: Synthesis of γ-Phenylthiocrotonate Esters
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The effects of functional groups near the migration origin in and PhS shifts are explored: an α-CO2R group prevents migration, α or β vinyl groups have only steric effects, alkynyl or CO2Et groups encourage rearrangement and provide routes to γ-phenylthio unsaturated esters and ketones.
- Brownbridge, Peter,Hunt, Paul G.,Warren, Stuart
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p. 1695 - 1706
(2007/10/02)
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- PYROLYSIS OF α-ACYL,α-THIO PHOSPHORANES THIOACETYLENES
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Pyrolysis of α-acyl,α-thio phosphoranes affords thioacetylenes in a good yield.The thio acethylenes are precursors of terminal and alkyl disubstituted acetylenes.
- Braga, Antonio L.,Comasseto, Joao V.,Petragnani, Nicola
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p. 1111 - 1114
(2007/10/02)
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- Selenium Heterocycles. XXXV. Synthesis and Pyrolysis of Aryloxy-, Arylthio-, and Arylseleno-1,2,3-selenadiazoles
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A series of 4-substituted-5-arylthio-1,2,3-selenadiazoles, 4-substituted-5-arylseleno-1,2,3-selenadiazoles and 4-aryloxymethyl-1,2,3-selenadiazoles were synthesized.Pyrolysis of these compounds afforded the corresponding acetylenes XI, XIII (X = S, Se) and XII, respectively.Oxidation of 4-substituted-5-arylthio-1,2,3-selenadiazoles (XIV) with m-chloroperbenzoic acid gave 4-substituted-5-arylsulfinyl-1,2,3-selenadiazoles (XV) and 4-substituted-5-arylsulfonyl-1,2,3-selenadiazoles (XVI).
- Shafiee, A.,Toghraie, S.,Aria, F.,Mortezaei-Zandjani, G.
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p. 1305 - 1308
(2007/10/02)
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- CINETIQUE ET MECANISME DE LA REACTION DE PROTOTROPIE DES COMPOSIES PROPARGYLIQUES, ALLENIQUES ET PROPYNYLIQUES PORTANT UN HETEROATOME (COLONNE Vb ET VIb)
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A detailed kinetic study of the prototropic rearrangement of the system RMCH2-CCHRM-CH=C=CH2RM-CC-CH3 where M=NR, O, S, Se is presented.Using deuterated substrates the nature of the reactive intermediates and, in the case of M=S, the activatio
- Pourcelot, G.,Cadiot, P.,Georgoulis, C.
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p. 2123 - 2128
(2007/10/02)
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