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Regiochemistry of copper(I)-mediated cyclization reactions of halo-dienamides
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Clark, Andrew J., Geden, Joanna V., Thom, Stephen and Wilson, Paul (2007) Regiochemistry of copper(I)-mediated cyclization reactions of halo-dienamides. Journal of Organic Chemistry, Vol.72 (No.15). pp. 5923-5926. doi:10.1021/jo070680p ISSN 0022-3263.
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Official URL: http://dx.doi.org/10.1021/jo070680p
Abstract
Reaction of 2-substituted dienamides with catalytic amounts of copper halide/tripyridylamine (TPA) furnishes either 5-exo or 6-endo products with the outcome dependent upon the radical initiating unit. Reaction of 3-substituted dienamides produces beta-lactams via a 4-exo cyclization with termination of the reaction occurring via either halogen atom transfer, trapping with oxygen, elimination, or radical-radical coupling depending upon the diene.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Journal of Organic Chemistry | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 0022-3263 | ||||
Official Date: | 20 July 2007 | ||||
Dates: |
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Volume: | Vol.72 | ||||
Number: | No.15 | ||||
Number of Pages: | 4 | ||||
Page Range: | pp. 5923-5926 | ||||
DOI: | 10.1021/jo070680p | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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