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Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds.
MedLine Citation:
PMID:  19072794     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes (VDCPs), 1, with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds have been thoroughly investigated. We found that pyrrolidine and 1,2,3,4-tetrahydroquinoline derivatives can be formed in good yields in the reactions of VDCPs 1 with ethyl (arylimino)acetates 2 by a [3+2] cycloaddition or intramolecular Friedel-Crafts reaction pathway. Based on these results, we found that activated carbon-nitrogen and nitrogen-nitrogen double-bond-containing compounds, such as N-toluene-4-sulfonyl (N-Ts) imines 5 and diisopropylazodicarboxylate (7), can also react with VDCPs 1 to give [3+2] cycloaddition products in moderate to good yields in the presence of a Lewis acid. When N-tert-butoxycarbonyl aldimine 9 was used as the substrate, six-membered cycloaddition products 10 and 11 were formed in moderate yields in the presence of a Brønsted acid, trifluoromethanesulfonic acid (TfOH). The reactions of VDCPs 1 with N-Ts-iminophenyliodinane (12) were also carried out in the presence of (CuOTf)(2)C(6)H(6) and it was found that nitrogen-containing indene derivatives 13 were obtained, rather than the aziridination products. Plausible mechanisms for all of these transformations are discussed, based on the obtained results.
Authors:
Jian-Mei Lu; Zhi-Bin Zhu; Min Shi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009  
Date Detail:
Created Date:  2009-01-14     Completed Date:  2009-02-24     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  963-71     Citation Subset:  -    
Affiliation:
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China.
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