Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.

Lucile Anthore; Shiguang Li; Lorenzo V. White; Samir Z. Zard

doi:10.1021/acs.orglett.5b02681

Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.: Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

Lucile Anthore ¹ Shiguang Li ¹ Lorenzo V. White ¹ Samir Z. Zard ¹

1 DCSO - Laboratoire de synthèse organique

Abstract : A simple radical-based route to gem-alpha-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et3N in methanol. In the case of certain substrates, it was possible to form shipped dienoic acid and methyl E,E-dienoates.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-01245804
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Submitted on : Thursday, December 17, 2015 - 4:32:36 PM
Last modification on : Thursday, February 7, 2019 - 5:16:36 PM

Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.: Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

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Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.: Application to the Synthesis of Z-Alkenoates and E,E-Dienoates

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