86726-10-5Relevant academic research and scientific papers
Palladium-Chatalyzed Reaction of 2-Vinyl-2,3-dihydrobenzofurans and Chroman with Nucleophiles
Hosokawa, Takahiro,Kono, Takanori,Uno, Toru,Murahashi, Shun-Ichi
, p. 2191 - 2194 (1986)
Reaction of 2,3-dihydro-2-vinylbenzofuran with nucleophiles (NaCH(COOEt)2 and PhNHCH3) in the presence of palladium catalysts such as Pd(PPh3)4 and PdCl2(PR3)2 (R=Ph and Et) gives 2-(2-butenyl)phenols (46-76percent yields) in which nucleophiles are incorporated into the methyl group of the butenyl moiety. 2-Vinyl-chroman undergoes the same type of reaction where only the palladium complex bearing PEt3 ligand is effective.The effectiveness of PEt3 ligand is also observed in the reaction of 2,3-dihydro-2-isopropenylbenzofuran with diethyl sodiomalonate leading to 3-ethoxycarbonyl-4-(2-methyl-1-propenyl)-2-chromanone.
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
Sartori, Giovanni,Bigi, Franca,Casiraghi, Giovanni,Casnati, Giuseppe
, p. 1761 - 1764 (2007/10/02)
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.
