28915-98-2Relevant academic research and scientific papers
Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues
Tan, Ayse,Kazancioglu, Mustafa Zahrittin,Aktas, Derya,Guendogdu, Oezlem,Sahin, Ertan,Horasan Kishali, Nurhan,Kara, Yunus
, p. 629 - 637 (2014)
Three new polysubstituted isoindole-1,3-diones were prepared from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydroisoindole-1,3-dione. The reaction of 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione with m-CPBA gave the corresponding epoxide. The triacetate derivative was obtained via cis-hydroxylation using OsO4, followed by acetylation. An aromatic derivative, a secondary reaction product, was also formed during the acetylation. Finally, a tricyclic derivative from 2-ethyl-5-hydroxy-3a,4,5,7a- tetrahydro-isoindole-1,3-dione was synthesized via dichloroketene addition under microwave irradiation. The exact structures of epoxide and tricyclic derivatives were determined by X-ray diffraction analysis. TUeBITAK.
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: The synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride
K?se, Aytekin,ünal, Asli,?ahin, Ertan,Bozkaya, U?ur,Kara, Yunus
, p. 931 - 936 (2019)
In this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione resulted in the formation of ylidenesulfamoyl chloride, whose exact configuration was determined by X-ray crystal analysis. We explain the mechanism of product formation supported by theoretical calculations.
Reaction enthalpy of nucleophilic substitution of ethyl iodide in acetonitrile and its mechanistic significance
Kondo, Yasuhiko,Tsukamoto, Tamio,Kimura, Naoko
, p. 1765 - 1769 (2007/10/03)
Enthalpies of reaction for nucleophilic substitution of ethyl iodide have systematically been determined in acetonitrile. Through the concurrent analysis of empirical correlations between the reaction enthalpies and the specific interaction enthalpies for relevant anions with those between the logarithmic rates and the specific interaction enthalpies, partial desolvation accompanying activation has been deduced to be the major contributor to activation thermodynamic parameters, while the propensity of the reacting central atom in the nucleophilic anion plays a crucial role in determining reaction thermodynamic parameters. Semi-empirical molecular orbital calculations have supported these ideas. The application of the Marcus equation to the analysis of reaction characteristics in these reactions is discussed.
Single-ion enthalpies of transfer as a scale of nucleophilic reactivity towards ethyl iodide in acetonitrile
Kondo, Yasuhiko,Tsukamoto, Tamio,Moriguchi, Chika
, p. 1699 - 1704 (2007/10/03)
Logarithmic rates for nucleophilic substitution towards ethyl iodide in acetonitrile correlate well with the specific interaction enthalpies for the relevant nucleophile, ΔHt,SIAN->MeOH(Nu-).According to the correlation, the bromide ion reaction falls into the imidide ion reaction series, while the chloride ion reaction falls into the carboxylate ion reaction series.The partial desolvation accompanying activation is crucial in determining the reactivity behaviour of the nucleophile anions.Semi-empirical quantum mechanical calculations (MNDO/PM3 and MNDO/PM3/COSMO) give reasonable estimates for the enthalpies of activation as well as for reaction enthalpies in acetonitrile.The relative location of the transition state, estimated on the basis of empirical analysis, is in accord with the variation of electronic charges for the exposed atoms, which has been evaluated through semi-empirical quantum mechanical procedures.
