UNUSUAL FRIEDEL-CRAFTS REACTIONS-VI. SYNTHESIS OF ETHYL 6-(2-HYDROXYPHENYL)-2-CARBETHOXY-4-HEXENOATES BY REACTION OF METAL PHENOLATES WITH DIETHYL 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLATES

DOI: 10.1016/S0040-4020(01)88684-1

Source and publish data:

Tetrahedron p. 1761 - 1764 (1983)

Update date:2022-08-05

Topics:

Authors:

Sartori, Giovanni

Bigi, Franca

Casiraghi, Giovanni

Casnati, Giuseppe

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Article abstract of DOI:10.1016/S0040-4020(01)88684-1

A mild synthesis of ethyl 6-(2-hydroxyphenyl)-2-carbethoxy-4-hexenoates (4) (SnCl4-promoted o-specific alkylation of potassium phenolates 1 with diethyl vinylcyclopropane-1,1-dicarboxylates 2) involves an oriented hexacoordinated substrate-reagent complex 3, accounting for both o-specific attack on the phenol, and 1,7-homoconjugate addition to the vinylcyclopropane.

Full text of DOI:10.1016/S0040-4020(01)88684-1

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