Base-catalyzed oligomerization of levoglucosenone |
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Authors: | Fred Shafizadeh Richard H Furneaux David Pang Thomas T Stevenson |
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Institution: | Wood Chemistry Laboratory, Department of Chemistry, University of Montana, Missoula, Montana U.S.A. |
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Abstract: | Heating levoglucosenone in aqueous triethylamine gives a dimer and two trimers in yields of 8, 18, and 56%, respectively. These compounds have been isolated crystalline, and their structures and stereochemistry have been investigated by 13C- and 1H-n.m.r. and other spectroscopic methods. These data indicate that the dimer is apparently formed by Michael addition to provide a C-3-C-4 linkage. Similar reactions provide a non-olefinic, C-3-C-4-linked, cyclic trimer and an olefinic, cyclic trimer containing two C-3-C-4 linkages and one C-2-C-3 linkage. |
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