不同位置取代基之雜環籠狀化合物之合成研究

Abstract

以鈉與環戊二烯反應形成環戊二烯陰離子,與鹵化烷作用,進行烷化反應, 在環戊二烯上接上不同取代基。若是以兩當量的鈉反應,再分別與 1,2-二 溴乙烷,1,4-二溴丁烷反應,得到 1,1-取代,spiro(2,4)-hepta-4,6- diene,以及 1,2-取代,5,6,7,8-tetrahydroindene 的環戊二烯衍生物。 衍生物分別與順式 1,4-烯二酮進行 Diels-Alder 反應,得到 endo加成物 為主產物,將 endo 加成物進行臭氧裂解,可以得到取代基在不同位置的四 氧雜環籠狀化合物。 Cyclopentadienyl anion,was obtained from the treatment of cyclo- adiene with sodium. The reaction of alkyl halides with cyclo- pentadienyl anion gave the alkyled product. Reaction of cyclopentadiene with 2 equivalents of sodium followed by addition of 1,2-dibromoethane and 1,4-dibromobutane gave 1,1- disubstituted product, spiro (2,4) hepta-4,6-diene, and 1,2- disubstituted product, 5,6,7,8-tetrahydroindene respectly. Reaction of these cyclopentadiene derivatives with cis enedione gave the corresponding endo adducts as the major products. Ozono- lysis of these endo adducts gave the corresponding heterocyclic cage compounds with substituent in different sites.