Comparison of Convenient Alternative Synthetic Approaches to 4-[(3-tert-Butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3,2′-adamantane]

Abstract

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.

Key words

1,2-dioxetanes - chemiluminescence - cross-coupling reactions - singlet oxygen - CIEEL

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