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  Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with quinone methides as Michael acceptors

Groszek, G., Blazej, S., Brud, A., Swierczynski, D., & Lemek, T. (2006). Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with quinone methides as Michael acceptors. Tetrahedron, 62(11), 2622-2630. doi:10.1016/j.tet.2005.12.040.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0013-D26F-F Version Permalink: https://hdl.handle.net/21.11116/0000-0004-9598-8
Genre: Journal Article

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https://www.sciencedirect.com/science/article/pii/S0040402005022088 (Publisher version)
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 Creators:
Groszek, G, Author
Blazej, S, Author
Brud, AJ1, Author           
Swierczynski, D, Author
Lemek, T, Author
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1External Organizations, ou_persistent22              

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 Abstract: Nucleophilic addition of α-halo-4-tolylsulfonyl methyl anions to quinone methides and subsequent reactions were studied. Three kinds of consecutive reaction products were isolated, depending on the substrate structures and reaction conditions. Two of them were identified as rearrangement products and one as the vicarious nucleophilic substitution (VNS) product. An unexpected 1,2-migration of the tosyl group was observed. The mechanism of the reactions is briefly discussed.

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 Dates: 2006-03
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1016/j.tet.2005.12.040
BibTex Citekey: GroszekBBSL2006
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Title: Tetrahedron
  Other : Tetrahedron : the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry
Source Genre: Journal
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Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 62 (11) Sequence Number: - Start / End Page: 2622 - 2630 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020