107735-50-2Relevant academic research and scientific papers
(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.
Methyl Effects in the Cyclization of γ-Epoxy Bis-Sulfones
Benedetti, Fabio,Berti, Federico,Fabrissin, Silvio,Gianferrara, Teresa,Risaliti, Amerigo
, p. 3530 - 3537 (2007/10/02)
A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes.Reaction rates are increased by methyl groups on the chain conne
SYNTHESIS WITH SULFONES XLIV. STEREOSELECTIVE PREPARATION OF EE 1,3-DIENES BY ELIMINATION OF BENZENESULFINIC ACID FROM E HOMOALLYLIC SULFONES.
Penhoat, C. Herve Du,Julia, M.
, p. 4807 - 4816 (2007/10/02)
The preparation of pure E and Z homoallylic 1,1-disulfones followed by the stereoselective reduction of one sulfonyl moiety afforded pure E and Z homoallylic sulfones respectively.Basic elimination with tBuOK in THF gave the corresponding 1,3-dienes in good yield.This reaction, highly stereoselective in the case of E homoallylic sulfones, has been used in the synthesis of (8E,10E) 8,10-dodecadienol, 10 and (9E)9,11-dodecadienol, 15, insect pheromone components.
