IRIS publication 43339435
Domino reaction between 2-acylfurans and diethyl azodicarboxylate: a combined experimental, theoretical, X-ray and dynamic NMR study
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TY - JOUR - Gonzalez-Rosende, ME,Sepulveda-Arques, J,Zaballos-Garcia, E,Domingo, LR,Zaragoza, RJ,Jennings, WB,Lawrence, SE,O'Leary, D - 1999 - January - Rna-A Publication of The Rna Society - Domino reaction between 2-acylfurans and diethyl azodicarboxylate: a combined experimental, theoretical, X-ray and dynamic NMR study - Validated - () - DIELS-ALDER REACTION STEREOCHEMISTRY FURANS - 73 - 79 - Treatment of 2-acetylfuran 6a with diethyl azodicarboxylate gave the cycloadduct 7,6,7-diethoxycarbonyl-6,7-diazas-oxabicyclo[3.2.1]oct3-en-2-one, whereas 5-methyl-2-formylfuran 6b reacted giving a simple hydrazide product derived from radical reaction on the formyl group. The structure of the bicyclic compound 7, established by NMR measurements, was confirmed by an X-ray crystallographic analysis. Variable temperature H-1 NMR and C-13 NMR studies of 7 indicate that this compound undergoes two distinct dynamic conformational changes with Delta G double dagger 10.2 and 13.1 kcal mol(-1) respectively. The reaction mechanism associated with the domino reaction between furfural I and dimethyl azodicarboxylate 9 to give the cycloadduct 10 has been theoretically characterized using ab initio methods at the RHF/6-31G* level. The reaction pathway can be described as a three-step process. The first step corresponds with a [4 + 2] cycloaddition between 1 and 9, while the two subsequent steps are associated with a structural isomerization of the initial formyl cycloadduct to a more stable final adduct. DA - 1999/01 ER -
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@article{V43339435, = {Gonzalez-Rosende, ME and Sepulveda-Arques, J and Zaballos-Garcia, E and Domingo, LR and Zaragoza, RJ and Jennings, WB and Lawrence, SE and O'Leary, D }, = {1999}, = {January}, = {Rna-A Publication of The Rna Society}, = {Domino reaction between 2-acylfurans and diethyl azodicarboxylate: a combined experimental, theoretical, X-ray and dynamic NMR study}, = {Validated}, = {()}, = {DIELS-ALDER REACTION STEREOCHEMISTRY FURANS}, pages = {73--79}, = {{Treatment of 2-acetylfuran 6a with diethyl azodicarboxylate gave the cycloadduct 7,6,7-diethoxycarbonyl-6,7-diazas-oxabicyclo[3.2.1]oct3-en-2-one, whereas 5-methyl-2-formylfuran 6b reacted giving a simple hydrazide product derived from radical reaction on the formyl group. The structure of the bicyclic compound 7, established by NMR measurements, was confirmed by an X-ray crystallographic analysis. Variable temperature H-1 NMR and C-13 NMR studies of 7 indicate that this compound undergoes two distinct dynamic conformational changes with Delta G double dagger 10.2 and 13.1 kcal mol(-1) respectively. The reaction mechanism associated with the domino reaction between furfural I and dimethyl azodicarboxylate 9 to give the cycloadduct 10 has been theoretically characterized using ab initio methods at the RHF/6-31G* level. The reaction pathway can be described as a three-step process. The first step corresponds with a [4 + 2] cycloaddition between 1 and 9, while the two subsequent steps are associated with a structural isomerization of the initial formyl cycloadduct to a more stable final adduct.}}, source = {IRIS} }
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AUTHORS | Gonzalez-Rosende, ME,Sepulveda-Arques, J,Zaballos-Garcia, E,Domingo, LR,Zaragoza, RJ,Jennings, WB,Lawrence, SE,O'Leary, D | ||
YEAR | 1999 | ||
MONTH | January | ||
JOURNAL_CODE | Rna-A Publication of The Rna Society | ||
TITLE | Domino reaction between 2-acylfurans and diethyl azodicarboxylate: a combined experimental, theoretical, X-ray and dynamic NMR study | ||
STATUS | Validated | ||
TIMES_CITED | () | ||
SEARCH_KEYWORD | DIELS-ALDER REACTION STEREOCHEMISTRY FURANS | ||
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START_PAGE | 73 | ||
END_PAGE | 79 | ||
ABSTRACT | Treatment of 2-acetylfuran 6a with diethyl azodicarboxylate gave the cycloadduct 7,6,7-diethoxycarbonyl-6,7-diazas-oxabicyclo[3.2.1]oct3-en-2-one, whereas 5-methyl-2-formylfuran 6b reacted giving a simple hydrazide product derived from radical reaction on the formyl group. The structure of the bicyclic compound 7, established by NMR measurements, was confirmed by an X-ray crystallographic analysis. Variable temperature H-1 NMR and C-13 NMR studies of 7 indicate that this compound undergoes two distinct dynamic conformational changes with Delta G double dagger 10.2 and 13.1 kcal mol(-1) respectively. The reaction mechanism associated with the domino reaction between furfural I and dimethyl azodicarboxylate 9 to give the cycloadduct 10 has been theoretically characterized using ab initio methods at the RHF/6-31G* level. The reaction pathway can be described as a three-step process. The first step corresponds with a [4 + 2] cycloaddition between 1 and 9, while the two subsequent steps are associated with a structural isomerization of the initial formyl cycloadduct to a more stable final adduct. | ||
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