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Synthesis of 5-alkyl-1-aryl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes as a chemiluminescent substrate with remarkable thermal stability

✍ Scribed by Masakatsu Matsumoto; Nobuko Watanabe; Noriko C. Kasuga; Fumiaki Hamada; Koji Tadokoro


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
232 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


6,

heptanes were synt~ized and their thermal stabilities and F--inclined ehenfilumineseent ~es wae examined Among the bicyclic dioxetm~s synthesized hae, me bearing a tert-bmyl or a 9-methylfluorenyl at the 5-position exhibited remarkable thermal stability.


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Singlet oxygenation of 4-tert-butyl-5-(3-tert-butyldimethylsiloxy)phenyl-3,3-dimethyl-2-phenyl-2,3-dihydrofuran (3a) in dichloromethane at 0Β°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 tetrab