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A facile and general route to 4-substituted-2 butenolides

✍ Scribed by Persephone Canonne; Mohamed Akssira; Gilles Lemay


Book ID
104244065
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
222 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis


Grignard reagents react with 7-oxabicycloC2.2.llhept-5-ene-2,3-dicarboxylic anhydride and produce in high yields the corresponding substituted bicycle-y-butanolides. These lactones produce the title compounds by retro Diels-Alder reaction during distillation. Previously, we have demonstrated that the action of di(bromomagnesio)alkanes with dicarboxylic cyclic anhydrides gave the corresponding spirolactones.'*' In a one-step reaction, this methodology was found to be general to most anhydrides with the exception of maleic anhydride which gave a mixture of several compounds.3 We describe herein a new and important aspect of this methodology which permits the synthesis of a series of bicyclobutanolides.


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