Investigations on the synthesis and chemiluminescence of novel 2-coumaranones - II

Author(s)

Schramm, Stefan ; Monteiro Leite Ciscato, Luiz Francisco ; Oesau, Pascal ; Krieg, Reimar ; Richter, Jan Frank ; Navizet, Isabelle ; Roca-Sanjuan, Daniel ; Weiss, Dieter ; Beckert, Rainer

• Document type: Journal article
• Source: ARKIVOC; v. N/A, p. 16-pg., 2015-01-01.

Abstract

The optimized one-pot synthesis of 16 new 2-coumaranones containing a carbamate side-chain is described. Furthermore, the quantum yields for the base-activated chemiluminescence in the presence of oxygen was determined for all compounds, with a maximum of 5.9 +/- 0.1 x 10(-2) E mol(-1), and the application of these compounds as substitutes for usual bioluminescent and chemiluminescent reagents in bioassays is anticipated. A preliminary mechanistic pathway is also suggested, making use of recent developments regarding aspects of organic chemiluminescence, in agreement with both experimental and theoretical data available on the induced 1,2-dioxetanone decomposition as well as with the high efficiency of this reaction. (AU)

• FAPESP's process: 12/02428-5 - Cyclic organic peroxides: synthesis and mechanism of reduction
• Grantee: Luiz Francisco Monteiro Leite Ciscato
• Support Opportunities: Regular Research Grants