Designing a catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate: Ring closure and isomerization control
The palladium-catalyzed ring closure of ortho-iodophenyl 3-butenoate to 4-methylcoumarin is in competition with the isomerization to the 2-butenoic ester; the latter reaction has been controlled by the appropriate use of ligands, solvents and neutralizing agents to the point that quantitative yields of the cyclic compound have been attained.
Catellani, Marta,Chiusoli, Gian Paolo,Marzolini, Giovanna,Rossi, Emanuela
p. 65 - 69
(2007/10/03)
A REINVESTIGATION OF THE CLAISEN REARRANGEMENT OF METHYL γ-ARYOXYCROTONATES; A CONVENIENT SYNTHESIS OF 3-ETHYLIDENEBENZOFURAN-2(3H)-ONES
The synthesis and Claisen rearrangement of methyl γ-aryloxyxcrotonates have been prepared and succesfully rearranged to a mixture of Z and E 3-ethylidenebenzofuran-2(3H)ones in refluxing ethylene glycol.
Sunitha, K.,Balasubramanian, K. K.
p. 3269 - 3278
(2007/10/02)
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