Kinetics and mechanism of the pyridine-catalyzed reaction of phenylselenenyl halides and some unsaturated alcohols

Bugarčić, Živadin D.; Petrović, Biljana; Rvović, Marina D.

doi:10.1016/j.molcata.2008.03.014

Cited by 9 publications

(2 citation statements)

References 41 publications

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“…As a part of our ongoing research, directed toward the intramolecular cyclization of unsaturated alcohols by means of phenylselenenyl halides as reagents, we have examined the chemo-, regio-, stereoselectivity and reaction kinetics as a function of substitution pattern at the double bond and at the carbinol carbon atom of the used alkenol substrate. The influence of some Lewis acids and bases as catalysts on mechanistic pathway and reaction rate has also been evaluated [12][13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Kinetic and mechanistic insight into Lewis base and acid-mediated phenylselenoetherification of 2,6-dimethyl-hept-5-en-2-ol

et al. 2015

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Mechanistic and kinetic aspects, as well as quantum chemical calculations, for the formation of a tetrahydrofurane ring by cyclization of the highly substituted alcohol-2,6-dimethyl-hept-5-en-2-ol with phenylselenohalides (PhSeCl and PhSeBr), in the presence of various Lewis bases (piperidine, triethylamine, pyridine and quinoline) and Lewis acids (CoCl 2 , SnCl 2 ) as additives were studied. The substituted tetrahydrofuran ring is common motif in many natural products, especially in bioactive marine macrolides. Due to the presence of additives in reactions, the high regioselectivity was achieved, and the tetrahydrofuran type of ether in all studied reactions was obtained in excess in regard to the six-membered cyclic ether. In addition, kinetic aspects of reactions mediated by Lewis bases were studied by UV-Vis spectroscopy (in THF, at 288 K), as reactions of pseudo-first-order. Obtained values for rate constants proved catalytic role of additives and indicated that the reaction rate depends on pKa values of used base as well as on their ability for formation of hydrogen bond with OH-alcohols group.

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Section: Introductionmentioning

confidence: 99%

Kinetic and mechanistic insight into Lewis base and acid-mediated phenylselenoetherification of 2,6-dimethyl-hept-5-en-2-ol

et al. 2015

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“…32 Due to its presence, which influences the cyclization, yields of ethers were almost quantitative. In continuation of that work, we have carried out a systematic kinetic study for determination of reaction mechanism 33 and additive influence on reaction rate. It was found that all the investigated reactions followed second order kinetics and rate constants depended on additive presence.…”

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Based catalyzed phenylselenoetherification of 6-methyl- hept-5-en-2-ol

Bugarčić

Rvović²,

Divac³

2010

Arkivoc

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The mechanism of phenylselenoetherification of 6-methylhept-5-en-2-ol in the presence of some bases (pyridine, triethylamine, quinoline, 2,2'-bipyridine) as catalysts was examined through kinetic study of the cyclization under pseudo-first order conditions, by UV-VIS spectrophotometry. The obtained values for the rate constants show that there is a good agreement between those constants and the basicity of the catalyst. The fastest reaction is the one using the strongest base (triethylamine) and the smallest rate constant corresponded to the use of the weakest base as catalyst (2, 2'-bipyridine).

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DFT study of the mechanism of the phenylselenoetherification reaction of linalool

2014

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Kinetics and mechanism of the pyridine-catalyzed reaction of phenylselenenyl halides and some unsaturated alcohols

Cited by 9 publications

References 41 publications

Kinetic and mechanistic insight into Lewis base and acid-mediated phenylselenoetherification of 2,6-dimethyl-hept-5-en-2-ol

Kinetic and mechanistic insight into Lewis base and acid-mediated phenylselenoetherification of 2,6-dimethyl-hept-5-en-2-ol

Based catalyzed phenylselenoetherification of 6-methyl- hept-5-en-2-ol

DFT study of the mechanism of the phenylselenoetherification reaction of linalool

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