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image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Canadian Journal of ...arrow_drop_down
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Canadian Journal of Chemistry
Article . 1991 . Peer-reviewed
License: CSP TDM
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Metallometallation of allenes: an exploratory study

Authors: Shankar M. Singh; Allan C. Oehlshlager;

Metallometallation of allenes: an exploratory study

Abstract

Reaction of either n-Bu3SnCu(CN)Li (8) or (n-Bu3Sn)2Cu(CN)Li2 (9) with 1,2-undecadiene gave 71–92% of a (Z/E) mixture of 1-tri-n-butylstannyl-2-undecene (27) accompanied by 8–32% of a mixture of (E)-2-tri-n-butylstannyl-2-undecene (28) and 2-tri-n-butylstannyl-1-undecene (29). When the above reactions were warmed to 0 °C, 28 and 29 were the major products. The mixed cuprates, 10–14, gave the mixtures rich in vinylstannanes, 28 and 29, along with 27. Addition of Sn—Al reagents, 15 and 16, or Sn—B reagents, 18 and 19, to 1,2-undecadiene in the presence of 5 mol% of CuCN or CoCl2•(PPh3)2 provided mixtures rich in vinylstannanes, 28 and 29. However, with 1 equiv. of CuCN, mixtures rich in allylstannanes 27 were obtained. Reaction of 5-hydroxy-1,2-pentadiene with the Sn—Al reagents, 15 and 16, gave 53–61% of a single 5-hydroxy-2-tri-n-butylstannyl-1-pentene (32) in the presence of 5 mol% of CoCl2•(PPh3)2. The stannylcopper adducts generated in the reaction of 1,2-undecadiene and 8 or 9 were treated with iodomethane to give 55–78% of a (Z/E: 67/33) mixture of 1-tri-n-butylstannyl-2-methyl-2-undecene (33). Addition of mixed silylcuprates, 21, 22, and 23, to 1,2-undecadiene gave mixtures rich in (E)-2-dimethylphenylsilyl-2-undecene (35) and 2-dimethylphenylsilyl-1-undecene (36). A rationale for the putative adducts' formation is also presented. Key words: Sn—Cu, Sn—Al, Sn—B reagents; putative adducts.

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
11
Average
Top 10%
Average
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