112185-48-5Relevant academic research and scientific papers
Bis(phenylsulfonyl)methane mediated synthesis of olefins: Via a halogen elimination and double bond migration
Hu, Yanwei,Jiang, Jing,Hu, Ying,Cai, Xin,Wang, Liudi,Chen, Shaohua,Zhang, Shilei,Zhang, Yinan
, p. 2619 - 2622 (2018/04/27)
An effective dehydrochlorination of bis(phenylsulfonyl)alkane to prepare alkene building blocks is developed. The elimination together with double bond migration results in a variety of β,γ-unsaturated bis(phenylsulfonyl)olefins in good yields with only E geometry. The following chemical diversification represents an easy and straightforward access to a series of alkene building blocks.
Pd-catalyzed borylative cyclisation of 1,7-enynes
Pardo-Rodriguez, Virtudes,Bunuel, Elena,Collado-Sanz, Daniel,Cardenas, Diego J.
supporting information, p. 10517 - 10519 (2012/11/07)
Reaction of a variety of 1,7-enynes with bis(pinacolato) diboron catalysed by Pd bis(trifluoroacetate) affords homoallylic and allylic boronates containing a six membered carbo- or heterocycle, by formation of C-C and C-B bonds
(Phenylsulfonyl)allenes as substrates for cycloaddition reactions: Intramolecular cyclizations onto unactivated alkenes
Padwa, Albert,Meske, Michael,Murphree, S. Shaun,Watterson, Scott H.,Ni, Zhijie
, p. 7071 - 7080 (2007/10/02)
The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO2- elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C1-C2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the π-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.
Intramolecular Ring Opening of Epoxides by Bis-Activated Carbanions. The Influence of Ring Size on Reactivity and Selectivity
Benedetti, Fabio,Berti, Federico,Fabrissin, Silvio,Gianferrara, Teresa
, p. 1518 - 1524 (2007/10/02)
A quantitative study on the effect of ring size in the intramolecular ring opening of epoxides by carbanions is described.Two series of substrates were examined: α,α-bis-sulfonyl ω-epoxides 1 and α-cyano-α-sulfonyl ω-epoxides 2; in each series the carbani
Rhodium(I)-Ctalyzed 'Metallo-Ene' Cyclizations/β-Eliminations
Oppolzer, Wolfgang,Fuerstner, Alois
, p. 2329 - 2337 (2007/10/02)
Octadienyl carbonates 5 provide cyclic 1,4-dienes 6 when treated with RhI complexes (1-10 mol-percent) at 80 deg C.Similar cyclization of cyclohexenyl acetate 8 affords cis-fused hexahydroindene 9.Analogues ring closures of nonadiene carbonate 10 yield preferably the cis-divinylpyrrolidine 11 with RhI catalysis but the trans-isomer 12 when catalyzed by Pd0.Azaoctadienyl carbonate 5a undergoes elimination with (5 mol-percent, 80 deg C) in MeCN giving acyclic triene 7.
The Base-catalysed Cyclisation of ο-Epoxy 1,1-Bis-sulphones. Reactivity and Selectivity as a Function of Ring Size
Benedetti, Fabio,Fabrissini, Silvio,Gianferrara, Teresa,Risaliti, Amerigo
, p. 406 - 407 (2007/10/02)
Cyclisation of terminal bis-sulphones can occur in two different modes; rates of ring closure for three- to seven-membered rings span over three orders of magnitude.
