α-Methoxy-benzylmetals: Original synthesis and reactivity

A. Krief; J. Bousbaa

doi:10.1016/S0040-4039(97)01410-X

α-Methoxy-benzylmetals: Original synthesis and reactivity

A. Krief, J. Bousbaa

Unite de recherche en chimie organique

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing 1-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF-OEt to produce the homologated tetrahydropyran derivative in good yield.

langue originale	Anglais
Pages (de - à)	6289-6290
Nombre de pages	2
journal	Tetrahedron Letters
Volume	38
Numéro de publication	35
Les DOIs	https://doi.org/10.1016/S0040-4039(97)01410-X
Etat de la publication	Publié - 1 sept. 1997

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10.1016/S0040-4039(97)01410-X

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title = "α-Methoxy-benzylmetals: Original synthesis and reactivity",

abstract = "Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing 1-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF-OEt to produce the homologated tetrahydropyran derivative in good yield.",

author = "A. Krief and J. Bousbaa",

year = "1997",

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doi = "10.1016/S0040-4039(97)01410-X",

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AU - Bousbaa, J.

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N2 - Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing 1-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF-OEt to produce the homologated tetrahydropyran derivative in good yield.

AB - Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing 1-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF-OEt to produce the homologated tetrahydropyran derivative in good yield.

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U2 - 10.1016/S0040-4039(97)01410-X

DO - 10.1016/S0040-4039(97)01410-X

M3 - Article

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EP - 6290

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

α-Methoxy-benzylmetals: Original synthesis and reactivity

Résumé

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