奎林稠合雙環〔2.2.2〕辛烯化合物，可使用雙環〔2.2.2〕辛-5-烯-2-酮與2-胺苯甲醛，在鹹性酒精溶液中進行弗利蘭德(Friedlander)反應而獲得。接著進行照光反應，無論使用二苯酮作為催化劑與否皆會因照光時間延長而造成產物分解。類似地，若使用3,6-二甲氧-2-胺苯甲醛，則所得的縮合產物，直接以硝酸銨鈰進行氧化反應可順利得到奎林-5,8-二酮親雙烯化合物，此化合物可作為親雙烯物，與1,3-環己二烯進行立體選擇行的[4+2]環化反應而形成多環烴。接著將隔間的雙環〔2.2.2〕辛烯，提昇至倍半雙環〔2.2.2〕辛烯探討。主要的四環酮合成步驟可以採用苯乙烯硫醯作為乙炔及乙烯的相當物和雙環〔2.2.2〕辛烯稠合的1,3-環己二烯部分進行〔4+2〕環化反應。同樣地再利用弗利蘭德反應即可達成奎林稠合倍半雙環〔2.2.2〕辛烯衍生物。 Bicyclo[2.2.2]octene bearing a quinoline fused at etheno bridge can be prepared from Friedlander reaction of bicyclo[2.2.2]oct-5-en-2-one with 2-aminobenzaldehyde. Photoreaction of the resulting quinoline with sensitizer and without sensitizer is described. Similarly, bicyclo[2.2.2]octene bearing a quinolin-5,8-dione is prepared by treatment of the bicyclic ketone with 3,6-dimethoxy-2-aminobenzaldehyde followed by conventional oxidation step. The pi-facial stereoselectivity on the activated carbon-carbon double bond of p-benzoquinone moiety is shown from the [4+2] cycloaddition with 1,3-cyclohexadiene followed byAlder's rule to give the anti-endo and syn-endo cycloadducts Extended work to the synthesis of quinoline fused sesquibicyclo[2.2.2]octenes is prepared from tetracyclo[6.2.2.23,6.02,7]tetradeca-9,13-dien-4-one with 2-aminobenzaldehyde in good yield. The key step for preparation of the required tetracyckic ketone in Friedlander reaction is the Diels-Alder cyclization of phenyl vinylsulphone, an ethylene equivalent, with the bicyclo[2.2.2]octene-fused cyclohexdiene ring.
