6212-77-7Relevant academic research and scientific papers
Studies related to the total synthesis of the sesquiterpene core of the pyrrolobenzoxazine natural products CJ-12662 and CJ-12663
Commandeur, Ma?gorzata,Commandeur, Claude,Paolis, Michael De,Edmunds, Andrew J.F.,Maienfisch, Peter,Ghosez, Léon
, p. 3359 - 3362 (2009)
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
Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides
Rozentsveig,Nikonova,Levanova,Korchevin
, p. 1264 - 1266 (2016/10/26)
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.
Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
Racine, Sophie,Hegedüs, Bence,Scopelliti, Rosario,Waser, Jér?me
supporting information, p. 11997 - 12001 (2016/08/16)
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.
Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- Or β- π-Addition?
Wodrich, Matthew D.,Caramenti, Paola,Waser, Jerome
, p. 60 - 63 (2016/01/12)
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
Mechanism and stereochemistry of domino reaction of 2,3-dichloroprop-1-ene with diphenyl dichalcogenides in the system hydrazine hydrate - KOH
Levanova,Vakhrina,Grabel'Nykh,Rozentsveig,Russavskaya,Albanov,Korchevin
, p. 1722 - 1727 (2015/05/20)
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.
Domino reaction of 2,3-dichloroprop-1-ene with diphenyl disulfide in the system hydrazine hydrate-potassium hydroxide
Levanova,Grabel'Nykh,Elaev,Russavskaya,Klyba,Albanov,Tarasova,Korchevin
, p. 1341 - 1344 (2013/09/23)
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
Prototropic rearrangement of 2-propynyl(methyl)amino, 2-propynyloxy, and 2-propynylsulfanyl derivatives of hetarenes under conditions of phase-transfer catalysis: Mechanism and limitations
Rubina,Fleisher,Abele,Popelis,Lukevits
, p. 963 - 967 (2007/10/03)
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
Rearrangements of 2-Phenylthioethanols with Alkenyl, Alkynyl, Ester, and Other Functionalised Alkyl Substituents at the Migration Origin: Synthesis of γ-Phenylthiocrotonate Esters
Brownbridge, Peter,Hunt, Paul G.,Warren, Stuart
, p. 1695 - 1706 (2007/10/02)
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.
PYROLYSIS OF α-ACYL,α-THIO PHOSPHORANES THIOACETYLENES
Braga, Antonio L.,Comasseto, Joao V.,Petragnani, Nicola
, p. 1111 - 1114 (2007/10/02)
Pyrolysis of α-acyl,α-thio phosphoranes affords thioacetylenes in a good yield.The thio acethylenes are precursors of terminal and alkyl disubstituted acetylenes.
