BASE-CATALYZED OLIGOMERIZATION OF LEVOGLUCOSENONE

Article abstract of DOI:10.1016/S0008-6215(00)81044-7

Heating levoglucosenone in aqueous triethylamine gives a dimer and two trimers in yields of 8, 18, and 56percent, respectively.These compounds have been isolated crystalline, and their structures and stereochemistry have been investigated by (13)C- and (1)H-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-linked, cyclic trimer and an olefinic, cyclic trimer containing two C-3-C-4 linkages and one C-2-C-3 linkage.