113303-06-3

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 23974-72-3 sodium phenylselenide 
• 1666-13-3 diphenyl diselenide 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 14660-38-9 Δ³-butenylmercury chloride 
• 33574-02-6 cyclopropylmethyl iodide 

Downstream Products

• 1386397-45-0 C₁₂H₁₄O₂Se 
• 125424-59-1 N-(3-Oxo-cyclohex-1-enyl)-N-(4-phenylselanyl-butyl)-acetamide 
• 125424-63-7 N-(3-Oxo-cyclopent-1-enyl)-N-(4-phenylselanyl-butyl)-acetamide 
• 125424-58-0 3-(4-Phenylselanyl-butylamino)-cyclohex-2-enone 
• 125424-62-6 3-(4-Phenylselanyl-butylamino)-cyclopent-2-enone 
• 74023-56-6 4-benzeneselenyl-1-butylamine 

Relevant academic research and scientific papers

Radical intermediates in the Zn-promoted Barbier-type alkylation of diphenyl diselenide in aqueous medium

The zinc promoted Barbier-type reaction of alkyl halides and diphenyl diselenide in aqueous medium leads to high yields of mixed selenides even in acidic medium. Especially the efficient formation of t-butylphenylselenide cannot be explained by nucleophil

SYNTHESIS OF N-PROTECTED SPIROAMINES RELATED TO NATURAL PRODUCTS USING RADICAL CYCLISATIONS

The use of radical cyclisations allows direct access to a family of azaspirocyclic ketones, including compounds having the azaspirononane, and azaspiroundecane structures which are found in the alkaloids cephalotaxine and histrionicotoxin.

Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals

The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.