
TY  - JOUR
A1  - Davidson, WJ 
A1  - Elix, JA 
T1  - Annelated furans. XI. The reactions of 2-vinylfurans with acetylenic esters
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 5
SP  - 1059
EP  - 1067
KW  - 
UR  - https://doi.org/10.1071/CH9731059 
N2  - In general dimethyl acetylenedicarboxylate and methyl propiolate have been found to react with 2-vinylfurans to give the corresponding dimethyl benzofuran-4,5-di-carboxylates and methyl benzofuran-4- carboxylates respectively. In several instances dimethyl acetylenedicarboxylate did not react exclusively with the exocyclic diene system of the 2-vinylfuran and here the corresponding dimethyl 3,6-epoxy-3-vinyl-3,6-dihydrophthalates were obtained by Diels-Alder addition to the furanoid diene system. At 80° 2-vinylfuran and dimethyl acetylenedicarboxylate formed the 1 : 2 adduct (11), the formation of which can be interpreted as involving an ene addition of a second mole of the acetylenic ester to the initially formed Diels-Alder adduct. 
ER  -

