TY - JOUR
T1 - Synthesis and photooxidation of furylthymines; chemiexcitation model studies
AU - Dannenberg, W.
AU - Feringa, Bernard
N1 - Relation: http://www.rug.nl/scheikunde/
date_submitted:2005
Rights: University of Groningen. Stratingh Institute
PY - 1984
Y1 - 1984
N2 - A method for the synthesis of 1-(5-methyl-2-furoyl)thymine (7) and 1-(5-methyl-2-furyl)thymine (8) is described. Trimethylsilyliodide catalysed addition of 5-methyl-2,4-bis(trimethylsilyloxy)pyrimidine (9) to 2-methyl-2,5-dihydro-2,5-dimethoxyfuran yielded the new thymine derivative 13. Photooxidations of 7 and 8 gave not the expected addition products but furan endoperoxides and hydroperoxides and the novel rearrangement product 1-(3-keto-1-butenyl)-thymine.
AB - A method for the synthesis of 1-(5-methyl-2-furoyl)thymine (7) and 1-(5-methyl-2-furyl)thymine (8) is described. Trimethylsilyliodide catalysed addition of 5-methyl-2,4-bis(trimethylsilyloxy)pyrimidine (9) to 2-methyl-2,5-dihydro-2,5-dimethoxyfuran yielded the new thymine derivative 13. Photooxidations of 7 and 8 gave not the expected addition products but furan endoperoxides and hydroperoxides and the novel rearrangement product 1-(3-keto-1-butenyl)-thymine.
U2 - 10.1002/recl.19841030603
DO - 10.1002/recl.19841030603
M3 - Article
SN - 1878-7096
VL - 103
SP - 192
EP - 196
JO - Recueil des Travaux Chimiques des Pays-Bas
JF - Recueil des Travaux Chimiques des Pays-Bas
IS - 6
ER -