Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one.

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TY  - JOUR
  - ZaballosGarcia, E,GonzalezRosende, ME,JordaGregori, JM,SepulvedaArques, J,Jennings, WB,OLeary, D,Twomey, S
  - 1997
  - July
  - Tetrahedron
  - Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one.
  - Validated
  - ()
  - 53
  - 9313
  - 9322
  - 2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. H-1 and C-13 NMR Studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to -90 degrees C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion. (C) 1997 Elsevier Science Ltd.
DA  - 1997/07
ER  - 
@article{V43339599,
   = {ZaballosGarcia,  E and GonzalezRosende,  ME and JordaGregori,  JM and SepulvedaArques,  J and Jennings,  WB and OLeary,  D and Twomey,  S },
   = {1997},
   = {July},
   = {Tetrahedron},
   = {Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one.},
   = {Validated},
   = {()},
   = {53},
  pages = {9313--9322},
   = {{2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. H-1 and C-13 NMR Studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to -90 degrees C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion. (C) 1997 Elsevier Science Ltd.}},
  source = {IRIS}
}
AUTHORSZaballosGarcia, E,GonzalezRosende, ME,JordaGregori, JM,SepulvedaArques, J,Jennings, WB,OLeary, D,Twomey, S
YEAR1997
MONTHJuly
JOURNAL_CODETetrahedron
TITLERing transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one.
STATUSValidated
TIMES_CITED()
SEARCH_KEYWORD
VOLUME53
ISSUE
START_PAGE9313
END_PAGE9322
ABSTRACT2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. H-1 and C-13 NMR Studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to -90 degrees C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion. (C) 1997 Elsevier Science Ltd.
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