1207993-63-2Relevant academic research and scientific papers
Synthesis of sulfanyl-, sulfinyl-, and sulfonyl-substituted bicyclic dioxetanes and their base-induced chemiluminescence
Watanabe, Nobuko,Kikuchi, Masato,Maniwa, Yuusuke,Ijuin, Hisako K.,Matsumoto, Masakatsu
supporting information; experimental part, p. 879 - 884 (2010/05/18)
(Chemical Equation Presented) The singlet oxygenation of 4-tert-butyl-3,3-dimethyl-5-(3-oxyphenyl)-2,3-dihydrothiophenes 5c-e bearing an acetoxy or methoxy group at the 2-position exclusively gave the corresponding sulfanylsubstituted bicyclic dioxetanes 2c-e, while that of 5a without 2-substituent mainly gave sulfoxide 11 alongwith a small amount of dioxetane 2a. These dioxetanes were sufficiently stable thermally to permit handling at room temperature. Sulfanyl-substituted dioxetanes, 2c and 2e, were further oxidized with m-chloroperbenzoic acid to afford the corresponding sulfinyl-substituted dioxetanes 3c, 3e and sulfonylsubstituted dioxetanes 4c, 4e. X-ray single crystallographic analysis was performed for 2c and 4e. Baseinduced decomposition of the dioxetanes in DMSO gave light with a maximum wavelength λmaxCL at 554 nmfor 2a and 565 nmfor 2e in moderate light yields,while sulfinyl-derivative 3e gaveweak light with λmaxCL = 795 nm and sulfonyl-derivative 4e gave very weak light with λmaxCL = 848 nm. 2010 American Chemical Society.
