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

Erick Leite Bastos; Luiz Francisco Monteiro Leite Ciscato; Dieter Weiss; Rainer Beckert; Wilhelm Josef Baader

doi:10.1055/s-2006-942357

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Synthesis 2006(11): 1781-1786
DOI: 10.1055/s-2006-942357

PAPER

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

Erick Leite Bastos^a, Luiz Francisco Monteiro Leite Ciscato^a, Dieter Weiss^b, Rainer Beckert^b, Wilhelm Josef Baader*^a
^a Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, Bl 12S, 05508-900 São Paulo, SP, Brazil
Fax: +55(11)30912371; e-Mail: wjbaader@iq.usp.br;
^b Institut für Makromolekulare Chemie und Organische Chemie, Friedrich-Schiller-Universität, Humboldtstraße 10, 07743 Jena, Germany

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Publication History

Received 25 November 2005
Publication Date:
05 May 2006 (online)

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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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