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

Organic & Biomolecular Chemistry
Pratik YadavRamendra Pratap

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.

References

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Citations

Aug 1, 2020·Organic & Biomolecular Chemistry·Ranjay ShawRamendra Pratap

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Methods Mentioned

BETA
X-ray
NMR
column chromatography

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