| Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements. | |
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MedLine Citation:
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PMID: 12585873 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis. |
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Authors:
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Annabelle L K Shi Shun; Erin T Chernick; Sara Eisler; Rik R Tykwinski |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 68 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2003 Feb |
Date Detail:
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Created Date: 2003-02-14 Completed Date: 2003-10-20 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 1339-47 Citation Subset: - |
Affiliation:
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Department of Chemistry, University of Alberta, Edmonton AB T6G 2G2, Canada. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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