1980
DOI: 10.1021/jo01305a021
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Ene reaction of triazolinediones with alkenes. 2. Kinetics and substituent effects

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1983
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Cited by 46 publications
(40 citation statements)
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“…Similar activation of dienophiles in H ‐donor solvents is well known for other types of reactions. Previously, the solvent effect on the rate of the number of reactions involving dienophile 1 has been considered, which makes it possible to compare the solvent effect on the rate of the studied ene reactions 1 + 2 → 3 and 1 + 4 → 5 with regard to the [2π+2σ+2σ]‐cycloaddition reaction of 1 with quadricyclane ( 7 ), ene reaction with 2‐methylbutene‐2 ( 14 ), [2π+2π]‐cycloaddition reaction of 1 with 2‐chloroethylvinyl ether ( 15 ), ene reaction between 1 and norbornene ( 9 ) with Wagner‐Meerwein rearrangement, ene reaction of 1 with trans ‐hexene‐3 ( 16 ), [4π+2π]‐cycloaddition reaction of 1 with anthracene ( 17 ), and [2π+2π]‐cycloaddition reaction of 1 with bisadamantylidene ( 10 ) (Equations ): trueright ln k()bold1+bold2=left()1.04±0.03· ln k()bold1+bold4()0.65±0.07;leftR2=0.9939,N=9trueright ln k()bold1+bold7=left()0.82±0.14· ln k()bold1+bold4+()0.13±0.29;leftR2=0.8515,N=8trueright ln k()bold1+bold15=left()0.52±0.03· ln k()bold1+bold4+()2.65±0.08;leftR2=0.9869,N=5trueright ln k()bold1+bold9=left…”
Section: Resultsmentioning
confidence: 99%
“…Similar activation of dienophiles in H ‐donor solvents is well known for other types of reactions. Previously, the solvent effect on the rate of the number of reactions involving dienophile 1 has been considered, which makes it possible to compare the solvent effect on the rate of the studied ene reactions 1 + 2 → 3 and 1 + 4 → 5 with regard to the [2π+2σ+2σ]‐cycloaddition reaction of 1 with quadricyclane ( 7 ), ene reaction with 2‐methylbutene‐2 ( 14 ), [2π+2π]‐cycloaddition reaction of 1 with 2‐chloroethylvinyl ether ( 15 ), ene reaction between 1 and norbornene ( 9 ) with Wagner‐Meerwein rearrangement, ene reaction of 1 with trans ‐hexene‐3 ( 16 ), [4π+2π]‐cycloaddition reaction of 1 with anthracene ( 17 ), and [2π+2π]‐cycloaddition reaction of 1 with bisadamantylidene ( 10 ) (Equations ): trueright ln k()bold1+bold2=left()1.04±0.03· ln k()bold1+bold4()0.65±0.07;leftR2=0.9939,N=9trueright ln k()bold1+bold7=left()0.82±0.14· ln k()bold1+bold4+()0.13±0.29;leftR2=0.8515,N=8trueright ln k()bold1+bold15=left()0.52±0.03· ln k()bold1+bold4+()2.65±0.08;leftR2=0.9869,N=5trueright ln k()bold1+bold9=left…”
Section: Resultsmentioning
confidence: 99%
“…This suggests that the volume of the activated complex of reactions 1 + 4 → 5 and 1 + 6 → 7 in toluene is smaller by 16% than that of the products 5 and 7 . The data available, showing the weak influence of the solvent polarity on the reaction rate, allow to exclude the solvent electrostriction in the solvation shell of the activated complex as the main cause resulting in this ratio: ∆ V ≠ corr /∆ V r − n > 1. This “abnormal” ratio (∆ V ≠ corr /∆ V r − n > 1) in the isopolar DARs was explained by different possibilities of the solvent molecules to fit the large steric hindered structures of the cyclic activated complex and cyclic adducts .…”
Section: Resultsmentioning
confidence: 99%
“…An extensive study of the products structure, the reaction rate and the solvent effect on the reaction of [4 + 2]‐cycloaddition of 1 with various 1,3‐dienes was presented . Practically, at the same time, the ene synthesis of 1 with various alkenes was initiated . N ‐allylurazole derivatives, the ene reaction products, are usually formed when the allyl hydrogen atom is present in alkene as well as α‐shift of the double bond in the product is possible …”
Section: Introductionmentioning
confidence: 99%
“…We observed only small variations of the ratio of products 3 and 4 with increase in solvent polarity for reactions carried out in diethyl ether, CHCl 3 , C 6 H 6 , CH 3 EXPERIMENTAL NMR spectra were recorded using a Varian Gemini BP spectrometer, UV spectra were recorded on a Specord spectrometer (Carl Zeiss Jena) using 10 mm cells.…”
Section: Introductionmentioning
confidence: 99%
“…Butler [3] carried out kinetic measurements for the reaction of 4-substituted -1,2,4-triazoline-3,5-diones including PTAD with different olefins.…”
Section: Introductionmentioning
confidence: 99%