67100-23-6Relevant academic research and scientific papers
dilithium as a Novel Cyclizing and Homologizing Reagent for Bifunctional Organic Substrates
Eisch, John J.,Dua, Suresh K.,Behrooz, Mohammad
, p. 3674 - 3676 (1985)
dilithium generated from methyl phenyl sulfone and 2 equiv of n-butyllithium in THF, reacts readily with a series of bifunctional organic substrates, such as dihalides, halo epoxides, halo carbonyls, halo nitriles, dicarbonyls, and α,β-unsaturated carbonyls, to give carbocyclic and homologous derivatives in good to excelent yields.
The Strain Limit in Intramolecular Nucleophilic Substitution
Jeffery, Stephen M.,Stirling, Charles J. M.
, p. 1617 - 1624 (2007/10/02)
Kinetics and products of reactions of sulfonyl-stabilised carbanions bearing ω-leaving groups have been examined.The intention was to explore the upper limit of strain that can be tolerated for intramolecular nucleophilic substitution in these systems and
γ- and δ-epoxy sulfones. Formation of different ring-sized products upon reaction with CH3MgI or LiN2
Decesare, John M.,Corbel, Bernard,Durst, Tony,Blount, John F.
, p. 1415 - 1424 (2007/10/02)
γ-Epoxy sulfones in which the epoxide function is terminal yield cyclopropylmethanol derivatives on reaction with methylithium or lithium diisopropylamide.In contrast, treatment of these epoxides with two equivalents of CH3MgI gives only cis-3-phenylsulfonylcyclobutanols.The cis-relationship between the OH and sulfonyl groups was proven in one instance by an X-ray stucture determination.Inernal γ-epoxy sulfones yield cyclopropylmethanols with all bases studied.All δ-epoxy sulfones studied furnished cis-3-phenylsulfonylcyclopentanols upon reaction with the Grignard reagent.These same epoxides gave either cyclopentanols or noncyclic products upon reaction with LDA; no cyclobutane ring containing products were obtained contrary to the expectations based on Stork's results with the corresponding epoxy nitriles (ref. 2).The mechanism of the Grignard-mediated reaction involves epoxide opening by iodide ion, α-sulfonyl Grignard formation, and, finally, cyclization.When LDA or CH3Li is used the products are formed by an intramolecular SN2 opening of the epoxide by an α-lithio sulfone.
