Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at -15 degreesC, leading to the quantitative generation of 3,5-dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non-functionalized and functionalized. alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5-substituted natural and non-natural resorcinols

Practical Generation of 3,5-Dimethoxybenzyllithium: Application to the Synthesis of 5-Substituted-Resorcinols / Azzena, Ugo Gavino; G., Dettori; M. V., Idini; Pisano, Luisa; G., Sechi. - In: APPLIED ORGANOMETALLIC CHEMISTRY. - ISSN 0268-2605. - 17:11(2003), pp. 851-855. [10.1002/aoc.531]

Practical Generation of 3,5-Dimethoxybenzyllithium: Application to the Synthesis of 5-Substituted-Resorcinols

AZZENA, Ugo Gavino;PISANO, Luisa;
2003

Abstract

Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at -15 degreesC, leading to the quantitative generation of 3,5-dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non-functionalized and functionalized. alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5-substituted natural and non-natural resorcinols
Practical Generation of 3,5-Dimethoxybenzyllithium: Application to the Synthesis of 5-Substituted-Resorcinols / Azzena, Ugo Gavino; G., Dettori; M. V., Idini; Pisano, Luisa; G., Sechi. - In: APPLIED ORGANOMETALLIC CHEMISTRY. - ISSN 0268-2605. - 17:11(2003), pp. 851-855. [10.1002/aoc.531]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/77768
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