The syntheses of 9-oxobenzomorphans 10 and 12 are described. Both products exist in the cyclic forms 11 and 13 respectively. Hydrobromide and oxalate salts of the 9-oxobenzomorphan 1 when crystallized from methanol form stable methylhemiketals 4 and 5. Bromination of 5 yielded benzomorphan 8 which on treatment with sodium hydroxide produced, via 10, the cyclic hemiketal 11. Reaction of 8 with sodium hydrogen sulfide afforded, via 12, the cyclic hemithioketals 13.
AbstractNew symmetrical disulfides together with the corresponding thiols bearing fluorescent end-groups have been synthesized as building-blocks for self-assembled monolayers (SAMs). The synthesis has been accomplished starting from aromatic nitrogen heterocycles in three steps. The conversion of the tosylated intermediate into the final disulfide is accomplished by use of sodium hydrogen sulfide (NaSH). Both products (thiols and disulfides) were isolated and characterized.
Synthesis of fluorescent long-chain thiols/disulfides as building-blocks for self-assembled monolayers preparation