Journal of Organic Chemistry p. 4360 - 4369 (1993)
Update date:2022-08-03
Topics:
Sura, Tushar P.
MacDowell, Denis W. H.
The inability to observe Cope rearrangement products at elevated temperatures for diethyl α-allyl-2-naphthalenemalonate (1) and diethyl α-allyl-9-phenanthrenemalonate (2) does not extend to the analogous systems resulting from replacement of the aromatic units by 2- and 3-benzothiophene nuclei.Thermal rearrangement of diethyl α-allyl-3-benzothiophenemalonate (5) at 215-255 deg C for 11 h produces the expected Cope rearrangement product diethyl 2-allyl-3-benzothiophenemalonate (10) (8percent) accompanied by trans- and cis-ethyl 2,3-dihydro-1-(ethoxycarbonyl)-1H-benzocyclopenta
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