Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Jun 24;67(25):4494-4497.
doi: 10.1016/j.tet.2011.04.038.

Superelectrophilic chemistry of amino-nitriles and related substrates

Erum K Raja  1 , Douglas A Klumpp
Affiliations

Superelectrophilic chemistry of amino-nitriles and related substrates

Erum K Raja et al. Tetrahedron. .

Abstract

The superacid-promoted Houben-Hoesch reactions of amino-nitriles and related compounds have been studied. The nitriles form dicationic electrophiles and react with benzene in fair to good yields (12-95%). The intermediate iminium ions may also be reduced to the benzylic amines by NaBH(4) or H(2).

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Calculated relative energies for superelectrophiles 29 and 30.
See this image and copyright information in PMC

References

    1. Hoesch K. Ber. Dtsch. Chem. Ges. 1915;48:1122.
    2. Houben J. Ber. Dtsch. Chem. Ges. 1926;59:2878.
    3. Smith MB, March J. March’s Advanced Organic Chemistry. 6th Ed. Wiley; NY: 2007. pp. 732–733.
    1. Sato Y, Yato M, Ohwada T, Saito S, Shudo K. J. Am. Chem. Soc. 1995;117:3037.
    2. Yato M, Ohwada T, Shudo K. J. Am. Chem. Soc. 1991;113:691.
    1. Klumpp DA. In: Recent Developments in Carbocation and Onium Ion Chemistry. Laali K, editor. American Chemical Society; Washington, DC: 2007. pp. 144–159. ACS Symposium Series 395.
    1. Gracias V, Ji Z, Akritopoulou-Zanze I, Abad-Zapatero C, Huth JR, Song D, Hajduk PJ, Johnson EF, Glaser KB, Marcotte PA, Pease L, Soni NB, Stewart KD, Davidsen SK, Michaelides MR, Djuric SW. Bioorg. Med. Chem. Lett. 2008;18:2691. - PubMed
    2. Raja AS, Pandeya SN, Panda SS, Stables JP. Pharm. Chem. J. 2007;41:302.
    1. Chung F, Tisne C, Lecourt T, Dardel F, Micouin L. Angew. Chem. Int. Ed. 2007;46:4489. - PubMed

LinkOut - more resources