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Synthesis 2013; 45(9): 1215-1226
DOI: 10.1055/s-0032-1318309
DOI: 10.1055/s-0032-1318309
paper
Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study
Further Information
Publication History
Received: 17 December 2012
Accepted after revision: 04 February 2013
Publication Date:
04 April 2013 (online)
Abstract
Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16–37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37–69%). The configuration of the resulting F- and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.
Key words
(perfluoroalkyl)-containing vinyldiazocarbonyl compounds - diazo transfer - Wittig reaction - 1,3-diketonesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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The starting methyl trifluorobutanoate 2f was prepared by a standard procedure.32a It can contain a quantity of the ethyl trifluorobutanoate formed due to base-catalyzed transesterification during Claisen condensation.32b In this case, the ethyl derivative impurity can also be present in the associated vinyl acetate 4f and further reaction products.