134518-91-5Relevant academic research and scientific papers
Comparison of convenient alternative synthetic approaches to 4-[(3-tert-butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3, 2′-adamantane]
Bastos, Erick Leite,Leite Ciscato, Luiz Francisco Monteiro,Weiss, Dieter,Beckert, Rainer,Baader, Wilhelm Josef
, p. 1781 - 1786 (2008/01/27)
The preparation of 4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro[1, 2-dioxetane-3,2′-adamantane] by two different approaches is described and the results are compared with previously reported data. The precursor olefin, 1-[3-(tert-butyldimethylsilyloxy)phenyl]-1-methoxy-2-spiroadamantylidene is obtained from 3-hydroxybenzaldehyde by both Horner-Wadsworth-Emmons and McMurry coupling reactions in 42% overall yield in both cases. 1,2-Dioxetane preparation by singlet oxygen addition, obtained through calcium peroxide diperoxohydrate thermolysis, is compared with conventional photooxygenation. Georg Thieme Verlag Stuttgart.
