35496-06-1

Upstream product

• 145134-41-4 Benzenesulfonic acid (1S,3R)-1-methyl-3-methylselanyl-3-phenyl-butyl ester 
• 145134-41-4 Benzenesulfonic acid (1R,3R)-1-methyl-3-methylselanyl-3-phenyl-butyl ester 
• 98-83-9 isopropenylbenzene 
• 74571-40-7 1-(2-methoxypent-4-en-2-yl)benzene 
• 89726-95-4 O-(methoxymethyl)-4-phenyl-1-penten-4-ol 
• 98-09-9 benzenesulfonyl chloride 
• 142060-72-8 (2R,4R)-4-Methylselanyl-4-phenyl-pentan-2-ol 
• 142060-72-8 (2S,4R)-4-Methylselanyl-4-phenyl-pentan-2-ol 
• 107432-61-1 (2-Bromo-1,2-dimethyl-cyclopropyl)-benzene 
• 145134-44-7 Benzenesulfonic acid (1S,3R)-1-methyl-3-phenyl-3-tributylstannanyl-butyl ester 

Relevant academic research and scientific papers

Zirconium-mediated conversion of homoallylic ethers into cyclopropane derivatives

Homoallylic ethers react with Cp2ZrCl2/2 n-BuLi reagent to afford cyclopropane derivatives. Cyclopropylcarbinyl-homoallyl rearrangements involving zirconium species are observed depending on the substrate structure.

A one-pot access to cyclopropanes from allylic ethers via hydrozirconation-deoxygenative ring formation

A synthetic method for the direct transformation of allylic ethers into mono-, di- and trisubstituted cyclopropanes is presented.

Stereochemical outcome of benzyllithiums synthesis from selenides

Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. γ-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane derivatives.

On the synthesis of aryl cyclopropanes from γ-benzenesulfonylalkyl tin derivatives and n-butyllithium

γ-Benzenesulfonyloxyalkyl tin derivatives readily available from γ-hydroxyalkyl selenides, n-butyllithium and trialkyl tin chlorides react with n-butyllithium and stereospecifically lead to aryl cyclopropanes. The transformation is quite general and allows the synthesis of α,β-di- and trisubstituted ones.

DIRECT CONVERSION OF ALKENES INTO METHYL-SUBSTITUTED CYCLOPROPANES USING AN ORGANOIRON ETHYLIDENE TRANSFER REAGENT

(η5-C5H5)(CO)2FeCH(CH3)SPh (8) serves as a quite useful reagent for the transfer of ethylidene groups to alkenes to give methyl-substituted cyclopropanes in good yields.The reaction is accomplished by allowing 8 to react with an alkylating agent such as trimethyloxonium tetrafluoroborate or methyl fluorosulfonate in the presence of the alkene substrate.The active ethylidene transfer reagent is apparently a sulfonium salt which is too reactive to be isolated under normal conditions.In all csases, cyclopropanes are obtained stereospecifically with respect to the configuration of the starting alkenes, and with certain classes of substrates such as cis-disubstituted alkenes, the reaction also occurs with very high syn-stereoselectivity.