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Paper | Special issue | Vol 97, No. 2, 2018, pp.1099-1115
Published online, 5th June, 2018
DOI: 10.3987/COM-18-S(T)93
Notable Difference between Tetrabutylammonium Fluoride and Organic Superbases as Triggers for the Chemiluminescent Decomposition of Bicyclic Dioxetanes Bearing a 4-(N-Phenylbenzimidazol-2-yl)-3-hydroxyphenyl Moiety

Nobuko Watanabe, Koh Kumagai, Rei Ohtuka, Ayu Wakatsuki, Hisako K. Ijuin, Yoshio Kabe, and Masakatsu Matsumoto*

*Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka 259-1293, Japan


Chemiluminescent decomposition of bicyclic dioxetanes 3a−3c bearing a 4-(N-phenylbenzimidazol-2-yl)-3-hydroxyphenyl moiety was effectively induced by organic superbases, BTPP [(tert-butylimino)tris-(pyrrolidino)phosphorene], TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene), MTBD(7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene), DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), and TMG (tetramethylguanidine), as well as TBAF in acetonitrile. Dioxetane 3c bearing a 3,5-dihydroxyphenyl moiety showed diverse chemiluminescence profiles depending on the base used. BTPP caused chemiluminescent decomposition due to the di-oxido anion of dioxetane, while DBU and TMG induced chemiluminescence from the mono-oxido anion of dioxetane. On the other hand, TBAF caused effective chemiluminescence due to the mono-oxido anion, though it acted as a stronger base than BTPP with regard to the rate of decomposition of 3c.