Synthese en reacties van dehydroadamtaan

This thesis deals with the synthesis of dehydroadamantane (tetracyclo [4, 3,1,02,4, 03.8] decane) (10) and of 2-mono and 2,4-disubstituted adamantanes (II and III). In chapter 1 a brief survey of the known methods for the preparation of adamantane and its derivatives is given. The synthesis of dehydroadamantane (10) by an intramolecular insertion reaction of ·carbena adamantane (1) is the subject of chapter 2. The requisite carbene was generated by pyrolysis of the lithiumsalt of the tosylhydrazone of adamantanone (17) (Bamford-Stevens reaction). An alternative synthesis involving oxidation of the hydrazone of adamantanone (13) with activated manganese dioxide did not lead to the desired dehydroadamantane (10) but rather to adamantylidene azine (14)