Transformations of cyclopropanol derivatives. 4. Alkyl substituent effects in ring-opening reactions of 6-methyl-5-hydroxytricyclo[4.4.0.01,5]decan-9-one

1977 ◽  
Vol 99 (6) ◽  
pp. 1965-1968 ◽  
Author(s):  
John D. Yordy ◽  
William Reusch
Keyword(s):  
Ring Opening ◽  
Substituent Effects ◽  
Alkyl Substituent ◽  
Ring Opening Reactions

Substituent Effects in Mechanochemical Allowed and Forbidden Cyclobutene Ring-Opening Reactions

2021 ◽  
Author(s):  
Cameron L. Brown ◽  
Brandon H. Bowser ◽  
Jan Meisner ◽  
Tatiana B. Kouznetsova ◽  
Stefan Seritan ◽  
...  
Keyword(s):  
Ring Opening ◽  
Substituent Effects ◽  
Ring Opening Reactions

Asymmetric Route to Pyridines Bearing a Highly Functionalized 2-Alkyl Substituent by Aziridine Ring-Opening Reactions

2007 ◽  
Vol 72 (10) ◽  
pp. 3859-3862 ◽  
Author(s):  
Diego Savoia ◽  
Giuseppe Alvaro ◽  
Romano Di Fabio ◽  
Andrea Gualandi
Keyword(s):  
Ring Opening ◽  
Alkyl Substituent ◽  
Aziridine Ring ◽  
Ring Opening Reactions

scholarly journals Asymmetric Route to Pyridines Bearing a Highly Functionalized 2-Alkyl Substituent by Aziridine Ring-Opening Reactions.

ChemInform ◽  
2007 ◽  
Vol 38 (37) ◽  
Author(s):  
Diego Savoia ◽  
Giuseppe Alvaro ◽  
Romano Di Fabio ◽  
Andrea Gualandi
Keyword(s):  
Ring Opening ◽  
Alkyl Substituent ◽  
Aziridine Ring ◽  
Ring Opening Reactions

Kinetic Study of Hydrolysis of Benzoates. Part XXVI. Variation of the Substituent Effect with Solvent in Alkaline Hydrolysis of Substituted Alkyl Benzoates

2006 ◽  
Vol 71 (11-12) ◽  
pp. 1557-1570 ◽  
Author(s):  
Vilve Nummert ◽  
Mare Piirsalu ◽  
Ilmar A. Koppel
Keyword(s):  
Kinetic Study ◽  
Alkaline Hydrolysis ◽  
Rate Constants ◽  
Substituent Effect ◽  
Substituent Effects ◽  
Alkyl Substituent ◽  
Solvent Parameters ◽  
Substituent Constants ◽  
Hydrolysis Of ◽  
Main Factor

The second-order rate constants k2 (dm3 mol-1 s-1) for the alkaline hydrolysis of substituted alkyl benzoates C6H5CO2R have been measured spectrophotometrically in aqueous 0.5 M Bu4NBr at 50 and 25 °C (R = CH3, CH2Cl, CH2CN, CH2C≡CH, CH2C6H5, CH2CH2Cl, CH2CH2OCH3, CH2CH3) and in aqueous 5.3 M NaClO4 at 25 °C (R = CH3, CH2Cl, CH2CN, CH2C≡CH). The dependence of the alkyl substituent effects on different solvent parameters was studied using the following equations:      ∆ log k = c0 + c1σI + c2EsB + c3∆E + c4∆Y + c5∆P + c6∆EσI + c7∆YσI + c8∆PσI     ∆ log k = c0 + c1σ* + c2EsB + c3∆E + c4∆Y + c5∆P + c6∆Eσ* + c7∆Yσ* + c8∆Pσ* .  ∆ log k = log kR - log kCH3. σI and σ* are the Taft inductive and polar substituent constants. E, Y and P are the solvent electrophilicity, polarity and polarizability parameters, respectively. In the data treatment ∆E = ES - EH2O , ∆Y = YS - YH2O , ∆P = PS - PH2O were used. The solvent electrophilicity, E, was found to be the main factor responsible for changes in alkyl substituent effects with medium. When σI constants were used, variation of the polar term of alkyl substituents with the solvent electrophilicity E was found to be similar to that observed earlier for meta and para substituents, but twice less when σ* constants were used. The steric term for alkyl substituents was approximately independent of the solvent parameters.

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