Synthesis and nuclear magnetic resonance spectra of some bridged polyhydromethanonaphthalenes. Bridge proton assignments

Study of Chemical Shift Variations in Tricyclic Urazoles with a Norbornane Skeleton

“…For example, a thorough study of all possible isomers of fully saturated norbornene dimers, such as 11 and 12, [18] shows that the endo protons are upfield of the exo partners in the all-exo isomer 11 but move downfield in 12 (see Table 1). Likewise, the chemical shift of the endo protons in the exo isomer of a variety of 10-substituted decahydrotrimethanonaphtalenes 13 [19] ranges from 1.00 to 1.40 ppm, always upfield of the exo protons (1.65 -1.93 ppm). It appears from Table 1 that the chemical transformation from the urazole 3 to a diazene 1 is very similar in its effect on chemical shifts of bridge protons to structural changes 8-7, 10-9, and 12-11 (from the endo-to the exo-isomer).…”

Carbon‐13 NMR spectra of tetracyclododecanes: Evidence for upfield δ and ε steric effects

“…They are also made up of two fused norbornyl rings and contain the same structural elements but in different spatial arrangements. Owing to molecular symmetry, the proton NMR spectra of ex+ endo-tetracyclo C6.2.1.1 3*6.02.7] dodeca-4-en-l l-ol (2A) 4 and exeexo-tetracyclo C6.2.1.1 376.02*7] dodeca-4-en-12-01 (3A)' are much simpler than that of lA, and have already been interpreted. We now report their l3C spectra and investigate some of the effects arising from their congested environments.…”

Nucleophilic addition to C,C double bonds. III. Chemical reactivity of 1endo, 4endo: 5exo, 8exo‐dimethano‐1,2,3,4,4a,5,8,8a‐octahydronaphthalen‐10syn‐ol and X‐ray structure analysis of its p‐nitrobenzoate

“…In order to study the applicability of this reaction mode on substrates with skeletons different from that of a, we investigated the behaviour in basic media of the known olefinic alcohol 13) [3] [4], as well as of the corresponding methylated novel analogue Z4), which promised to be good candidates as well:…”

“…Battiste el al. [3], who had synthesized 1 for the first time, did not succeed in isolating it as pure compound. Attempted purification by adsorption chromatography5) yielded the cyclic ether 3.…”

“…For our own studies we have synthesized the secondary alcohol 1 according to the procedure described by Battiste et al [3], and the hitherto unknown tertiary alcohol 2 from the same key intermediate ketone 5 [3] by addition of methyl lithium. It is noteworthy that both these alcohols 1 and 2 remained stable during our chromatographic purification under neutral conditions.…”