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Birch reduction with lithium/trimethylsilyl chloride

An interesting alternative to the Birch reduction with useful synthetic potential is provided by reductive silylation. Benzene, on treatment with lithium metal and trimethylsilyl chloride in THF for a pro-... [Pg.517]

Birch reduction of indole with lithium metal in THF in the presence of trimethylsilyl chloride followed by oxidation with p-benzoquinone gave l,4-bis(trimethylsilyl)indoIe (106). This is readily converted in two steps into l-acetyl-4-trimethylsilylindole. Friedel-Crafts acylation of the latter compound in the presence of aluminum chloride yields the corresponding 4-acylindole (107) (82CC636). [Pg.61]

Radical anions from aromatics which are intermediates in Birch-type reductions were prepared sonochemically. Pyridine, quinoline, and indole sonicated with lithium in THF in the presence of trimethylsilyl chloride yield the bis-TMS dihydroaromatics, which can be reoxidized, by air or benzoquinone, in a rapid and easy method to prepare silyl-substituted aromatics. The procedure was extrapolated to phenols (Eq. 6). ... [Pg.182]


See also in sourсe #XX -- [ Pg.52 ]




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1 -Trimethylsilyl lithium

Birch

Birch reduction

Birching

Chlorides reduction

Lithium Birch reduction

Lithium reductions

Trimethylsilyl chloride

With lithium, reduction

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