The allylic azide rearrangement

Achieving selectivity

Alina K. Feldman, Benoît Colasson, K. Barry Sharpless, Valery V. Fokin

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

Allylic azides undergo a rapid [3.3]-sigmatropic rearrangement which results in dynamic equilibrium of several isomers. Thus, reactions of allylic azides usually result in mixtures of products. However, even small differences in reactivity of the isomeric allylic azides can be amplified to result in a single product in good to excellent yields. For example, the Cu(I)-catalyzed cycloaddition with alkynes selectively captures primary and secondary allylic azide isomers, whereas MCPBA epoxidation favors isomers which contain more electron-rich double olefins.

Original languageEnglish
Pages (from-to)13444-13445
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number39
DOIs
Publication statusPublished - 5 Oct 2005
Externally publishedYes

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Azides
Isomers
Epoxidation
Cycloaddition
Olefins
Alkynes
Cycloaddition Reaction
Alkenes
Electrons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Feldman, A. K., Colasson, B., Sharpless, K. B., & Fokin, V. V. (2005). The allylic azide rearrangement: Achieving selectivity. Journal of the American Chemical Society, 127(39), 13444-13445. https://doi.org/10.1021/ja050622q

The allylic azide rearrangement : Achieving selectivity. / Feldman, Alina K.; Colasson, Benoît; Sharpless, K. Barry; Fokin, Valery V.

In: Journal of the American Chemical Society, Vol. 127, No. 39, 05.10.2005, p. 13444-13445.

Research output: Contribution to journalArticle

Feldman, AK, Colasson, B, Sharpless, KB & Fokin, VV 2005, 'The allylic azide rearrangement: Achieving selectivity', Journal of the American Chemical Society, vol. 127, no. 39, pp. 13444-13445. https://doi.org/10.1021/ja050622q
Feldman, Alina K. ; Colasson, Benoît ; Sharpless, K. Barry ; Fokin, Valery V. / The allylic azide rearrangement : Achieving selectivity. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 39. pp. 13444-13445.
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