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Synthesis 1985; 1985(12): 1118-1120
DOI: 10.1055/s-1985-31444
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Expedient Synthesis of 1,3-Cyclobutanedione via Thermal Dimerization of t-Butoxyethyne

Miquel A. Pericàs* , Fèlix Serratosa, Eduard Valenti
  • *Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1, 08028-Barcelona, Spain
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Publication Date:
27 September 2002 (online)

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A new, short, and efficient synthesis of 1,3-cyclobutandione consists of the therma conversion of t-butoxyethyne into 3-t-butoxycyclobutenone (the first example of cyclobutenone formation from an unsubstituted acetylenic monoether) followed by cleavage of the t-butyl group with trifluoroacetic acid. The 62% overall yield is much higher than that of the previously described procedure.