PART I: DIELS-ALDER REACTIONS OF HETEROSUBSTITUTED DIENES AND DIENOPHILES. PART II: ENAMINES AND IMINIUM SALTS FROM AMIDO-ACIDS.

The Diels-Alder reaction of 3-carbomethoxy-2,5-dihydrothiophenes with butadiene or isoprene yielded bicyclic thiolanes. The isomeric distribution of the adducts was assigned using cmr data. 3-Acylamino-2,5-dihydrothiophenes were oxidized to sulfones and formed dienes by thermal sulfur dioxide elimination. Heating these sulfones in the presence of maleic anhydride yielded the Diels-Alder adducts in good yields. The cycloaddition reaction of diethyl (alpha)-carbomethoxyvinylphosphonate with isoprene yielded the adduct in 95% yield and as one isomer. An attempt to prepare (alpha)-carbomethoxyvinylphosphonic acid diamide which could be used as a dienophile in the Diels-Alder reaction was unsuccessful. C- and N-((omega)-carboxyalkyl) lactams were prepared and distilled with soda-lime to form bicyclic enamines or imines. The method allows the preparation of bicyclic enamines with nitrogen at the bridgehead position as well as with nitrogen in the (alpha)-position. The formation of their iminium salts is also reported.Dept. of Chemistry and Biochemistry. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis1983 .P555. Source: Dissertation Abstracts International, Volume: 44-09, Section: B, page: 2757. Thesis (Ph.D.)--University of Windsor (Canada), 1983