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Paper Information

Journal:   JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)   2014 , Volume 11 , Number 4; Page(s) 1021 To 1026.
 
Paper: 

FACTORS AFFECTING THE COMPETITIVE REDUCTION OF 8,8-DIMETHYLNAPHTHALENE-1,4,5 (8H)-TRIONE IN A DIELS–ALDER CYCLOADDITION WITH HYDROXYSULFINYLDIENES

 
 
Author(s):  ALMODOVAR IRIUX, CARDONA WILSON, DELGADO CASTRO TOMAS, ZAPATA TORRES GERALD, CAROLI REZENDE MARCOS, ARAYA MATURANA RAMIRO
 
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Abstract: 

Competing reduction and cycloaddition products were formed in the reaction of 8,8-dimethylnaphthalene-1,4,5 (8H)-trione with a hydroxysulfinyldiene. The ratio of reduction to cycloaddition products depended on the stereochemistry of the diene and on the solvent employed, being higher in ethanol than in benzene. The ratio was also affected by the addition of Lewis acids, decreasing in the order BF3 = Al2O3 > MgCl2 > ZnCl2. The results help to explain and predict the occurrence of these competing processes in Diels–Alder cycloadditions involving quinonedienophiles.

 
Keyword(s): DIELS–ALDER, CYCLOADDITION, REDUCTION, QUINONE, SULFINYLDIENES
 
 
References: 
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Click to Cite.
APA: Copy

ALMODOVAR, I., & CARDONA, W., & DELGADO CASTRO, T., & ZAPATA TORRES, G., & CAROLI REZENDE, M., & ARAYA MATURANA, R. (2014). FACTORS AFFECTING THE COMPETITIVE REDUCTION OF 8,8-DIMETHYLNAPHTHALENE-1,4,5 (8H)-TRIONE IN A DIELS–ALDER CYCLOADDITION WITH HYDROXYSULFINYLDIENES. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), 11(4), 1021-1026. https://www.sid.ir/en/journal/ViewPaper.aspx?id=403376



Vancouver: Copy

ALMODOVAR IRIUX, CARDONA WILSON, DELGADO CASTRO TOMAS, ZAPATA TORRES GERALD, CAROLI REZENDE MARCOS, ARAYA MATURANA RAMIRO. FACTORS AFFECTING THE COMPETITIVE REDUCTION OF 8,8-DIMETHYLNAPHTHALENE-1,4,5 (8H)-TRIONE IN A DIELS–ALDER CYCLOADDITION WITH HYDROXYSULFINYLDIENES. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS). 2014 [cited 2021May11];11(4):1021-1026. Available from: https://www.sid.ir/en/journal/ViewPaper.aspx?id=403376



IEEE: Copy

ALMODOVAR, I., CARDONA, W., DELGADO CASTRO, T., ZAPATA TORRES, G., CAROLI REZENDE, M., ARAYA MATURANA, R., 2014. FACTORS AFFECTING THE COMPETITIVE REDUCTION OF 8,8-DIMETHYLNAPHTHALENE-1,4,5 (8H)-TRIONE IN A DIELS–ALDER CYCLOADDITION WITH HYDROXYSULFINYLDIENES. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), [online] 11(4), pp.1021-1026. Available: https://www.sid.ir/en/journal/ViewPaper.aspx?id=403376.



 
 
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