Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes?
Organic & Biomolecular Chemistry Pub Date: 2018-07-10 DOI: 10.1039/C8OB01270A
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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