Studies in peri-naphthalenes
Degree GrantorUniversity of Canterbury
Degree NameDoctor of Philosophy
1,2,3,4,7,8,9,10-Octahydrodicyclohepta[de,ij]naphthalene (17) and 2,3,6,7,8,9-hexahydro-lH-cyclohepta[gh] phenalene (46) have been prepared via benzsuberone (22), the tricyclic ketone 1, 2, 3, 7, 8, 9, 10,10a-octahydrocyclohepta[de]naphthalene (14), and the tetracyclic ketones 1-oxo- 1, 2, 3, 4, 4a, 5, 6, 6a,7, 8, 9, 10-dodecahydrodicyclohepta[de,ij] naphthalene (30) and 1-oxo-2,3,6,7,8,9-hexahydro-lH-cyclohepta[gh]phenalene (45), respectively. 5,6,7,8-Tetrahydrocyclohepta[fg]acenaphthene (57) was also prepared, by an improved method. The dicycloheptanaphthalene 17 and the cycloheptaacenaphthene 57, along with the tricyclic ketone 14 and the carbocyclic benzenes indan (64), tetralin (65), and benzsuberan (66) were reacted with mixtures of fuming nitric acid and acetic anhydride, and the resulting nitro-acetoxy adducts were isolated. The evidence for the structure of the hydrocarbons, their precursors, and their nitro acetoxy adducts is discussed, and mechanisms are suggested for their formation.