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Reaction of 3-Halogeno-2H-1-benzopyran-2-ones with Organometallic Compounds. Synthesis of 4-Alkyl-2H-1-benzopyran-2-ones. X-Ray Molecular Structure of 3-Bromo-3,4-dihydro-4-isopropylcoumarin

DOI: 10.1039/P19910000203

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 203 - 210 (1991)

Update date:2022-09-26

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Authors:

Alberola, AngelAlberola, Angel

Calvo, BlancaCalvo, Blanca

Ortega, Alfonso GonzalezOrtega, Alfonso Gonzalez

Vicente, MartinaVicente, Martina

Granda, Santiago G.Granda, Santiago G.

Van der Maelen, Juan F.Van der Maelen, Juan F.

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Article abstract of DOI:10.1039/P19910000203

3-Halogeno-2H-1-benzopyran-2-ones react with magnesium, lithium, aluminium and copper derivatives to give 3,4-dihydrocuomarins and 3-(o-hydroxyphenyl)propenols as major products.The nature and the ratio of the products in the final mixture depend on the solvent and on the organometallic reagent.Grignard derivatives yield 1,4-monoalkylation compounds in tetrahydrofuran (THF) or 1,2-dialkylation derivatives in toluene.In some cases the dehalogenation competes with the 1,2-alkylation process in the reactions with alkyllithiums.The presence of the halogen at C-3 increases the reductive ability of organoaluminiums.In general, the reaction with lithium dialkylcuprates leads to complex mixtures of products.The 4-alkyl-3-halogeno-3,4-dihydrocuomarins obtained undergo dehydrohalogenation easily, and lead to 4-alkylcuomarins in good yields.The tandem alkylation-dehydrohalogenation of 3-halogeno-2H-1-benzopyran-2-ones constitutes a versatile synthesis of 4-alkylcuomarins.

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Product name:(Z)-3-butyl-1-(o-hydroxyphenyl)hept-1-en-3-ol

Cas No:133380-31-1

133380-31-1

R&D Labs maybe for 133380-31-1

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