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Synthesis 2010(7): 1188-1194  
DOI: 10.1055/s-0029-1219233
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bromine-Induced Facile Synthesis of Butenolides and Spirobutenolides from Sterically Congested Tetrasubstituted Dialkyl Alkylidene Succinates

Ramesh M. Patel, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
Fax: +91(20)25902629; e-Mail: np.argade@ncl.res.in;
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Publikationsverlauf

Received 26 November 2009
Publikationsdatum:
20. Januar 2010 (online)

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Abstract

Starting from sterically congested tetrasubstituted dialkyl alkylidene succinates, facile general approach to several dialkyl substituted butenolides and spirobutenolides with the generation of quaternary carbon center has been demonstrated via bromine-induced dealkylative regioselective intramolecular cyclization and dehydrobromination pathway. The mechanistic aspects involved in the formation of butenolides have been also described in brief.

Key words

alkylidene succinates - bromine - intramolecular cyclizations - butenolides - spirobutenolides

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