M. Matsumoto, Yoshihiro Ito, Jyunya Matsubara
Mar 18, 2001
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Singlet oxygenation of 4- tert -butyl-5-(3- tert -butyldimethylsiloxy)phenyl-3,3-dimethyl-2-phenyl-2,3-dihydrofuran ( 3a ) in dichloromethane at 0°C gave a 95:5 mixture of stereoisomeric dioxetanes ( anti - 1a ) and ( syn - 1a ). The isomer ( anti - 1a ) was more stable thermally than syn - 1a . On treatment with tetrabutylammonium fluoride in DMSO or acetonitrile, both isomeric dioxetanes emitted intense blue light. Chemiluminescence efficiency ( Φ CL ) of anti - 1a was considerably higher than that of syn - 1a ; nevertheless, both of them gave the very same couple of two carbonyl fragments ( 2a ). A methyl-analog ( 1b ) was also synthesized and its chemiluminescent properties were examined.