Synthesen von Tricyclo4,8>decan (2-Homobrendan)

Article abstract of DOI:10.1002/hlca.19800630415

Three different approaches to tricyclo<5.2.1.0^4,8>decane (5) (and derivatives thereof), one of the 19 isomeric hydrocarbons of the 'adamantaneland', are described: 1) Cyclization of properly functionalized bicyclo<3.2.1>octanes as 32 (cyclialkylation), 40 + 42 (thermocyclization) and 44 + 45 (photocyclization); 2) Silver(I)-ion catalyzed rearrangement of 5,7- and 5,10-Dehydroprotoadamantane (63 and 64, respectively) yielding tricyclo<5.2.1.0^4,8>dec-2- (39) and -5-ene (59), respectively; 3) Thermal eliminative rearrangement of the 10endo-p-toluenesulfonate and -methanesulfonate of protoadamantane (71 and 72) and protoadamant-4-ene (76 and 77), respectively, yielding tricyclo<5.2.1.0^4,8>dec-2-ene (39) and -2,5-diene (15), respectively.