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Issue 30, 2018
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Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes

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Abstract

A base controlled regioselective 1,6-cyanoallylation of suitably functionalized 2H-pyran-2-ones has been demonstrated for the synthesis of various multi-substituted benzenes through a tandem process. We observed that lithium hydroxide provides a major product from α-attack and a minor product from γ-attack of allyl cyanide, while the use of sodium hydride as a base exclusively provides the product by γ-attack of allyl cyanide. We have also performed NMR experiments to understand the mechanistic pathway. The structure of the compound was confirmed by single crystal X-ray analysis.

Graphical abstract: Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes

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Publication details

The article was received on 29 May 2018, accepted on 10 Jul 2018 and first published on 10 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01270A
Citation: Org. Biomol. Chem., 2018,16, 5465-5473
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    Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes

    P. Yadav, R. Shaw, A. Elagamy, A. Kumar and R. Pratap, Org. Biomol. Chem., 2018, 16, 5465
    DOI: 10.1039/C8OB01270A

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