56625-01-5

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 123283-02-3 O-but-3-en-1-yl Se-phenyl selenocarbonate 
• 930-68-7 cyclohexenone 
• 94-36-0 dibenzoyl peroxide 

Relevant academic research and scientific papers

Liquid phase oxidation of alkenes with nitrous oxide to carbonyl compounds

A variety of substrates including linear, cyclic, heterocyclic alkenes and their derivatives were tested in the liquid phase non-catalytic oxidation with nitrous oxide (N2O). The structure and composition of the alkenes have a significant effect on the reaction selectivity. With many alkenes, N 2O oxidation provides a selective way for the preparation of carbonyl compounds. The generation of carbene (or diazomethane) species is a remarkable feature of the oxidation of terminal alkenes.

N,S-Dimethyldithiocarbamyl oxalates as precursors for determining kinetic parameters for oxyacyl radicals

N,S-Dimethyldithiocarbamyl oxalates (e.g.6, 10) are novel, readily prepared precursors to alkyloxyacyl radicals 1 that are more suitable for kinetic studies than existing precursors; 10 has allowed the determination of accurate rate data for the cyclization of the butenyloxyacyl radical 5 (kc = 1.2 × 107 s-1 at 21 °C). This journal is

Thermal and induced decompositions of N′-alkoxycarbonyldihydropyridines: End product analysis and EPR spectra of azacyclohexadienyl radicals

Hydrogen abstraction from N-alkoxycarbonyldihydropyridines generated azacyclohexadienyl radicals (pyridinyl radicals) which are characterised by EPR spectroscopy. In the presence of peroxide initiators, N-alkoxycarbonyl-1,2-dihydropyridines decomposed with production of pyridine, the corresponding alkyl formate, alkyl benzoate and alkanol being formed as the major products. Absence of cyclised products in experiments with substrates containing hex-5-enyl, pent-4-enyloxy etc. units demonstrates that radical production must be minor and that N-alkoxycarbonylazacyclohexadienyl radicals do not readily undergo ss-scission of the exocyclic N-C bond. The most probable mechanism is a direct 1,2-elimination of formate. The alcohols which accompanied the other products are probably formed by hydrolysis of the formates and benzoates. Analogous chemistry is displayed by N-alkoxycarbonyl-1,4-dihydropyridines at higher temperatures where 1,4-elimination of formate is too rapid for homolytic radical production to compete.

Synthesis of γ- and δ-Lactones by Free-Radical Annelation of Se-Phenyl Selenocarbonates

A general method for the synthesis of γ- and δ-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described.This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction.Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield.Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

Homolytic cyclization of O-alkenyl-Se-phenylselenocarbonates. Synthesis of lactones

O-Alk-3-enyl- and O-alk-4-enyl-Se-phenylselenocarbonates undergo regio-specific exo cyclization to the corresponding γ- and δ-lactones on treatment with tri-n-butylstannane and AIBN.