Tetrahedron Letters p. 5917 - 5920 (1987)
Update date:2022-08-05
Topics:
Apeloig, Yitzhak
Arad, Dorit
Kapon, Moshe
Wallerstein, Mercedes
The stereochemistry of the Diels-Alder reactions of 3 cyclopropenes was determined unequivocally by X-ray and NOE studies.Tetrachlorocyclopropene yields exo-adducts with (E)-1-R-1,3-butadiene (R=OCH3, OCOCH3, OSiMe3), with 1,4-diphenylbutadiene and with furan. 1,2-bromochlorocyclopropene yields with (E)-1-R-butadienes (R=OCH3, OSiMe3) endo:exo-adducts in a ratio of 9:1.Cyclopropene + 1-methoxybutadiene yield only the endo-adduct.
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