Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels-Alder reaction

Article abstract of DOI:10.1016/S0022-328X(98)01175-9

Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels-Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation-mesylation-reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride produced pure olefins in good yields.