78710-64-2Relevant academic research and scientific papers
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.
