N,N,N′-Trialkyl-1,8-diaminonaphthalenes: convenient method of preparation from protonated proton sponges and the first X-ray information

1,8‐Bis(dialkylamino)‐4,5‐dinitronaphthalenes and 4,5‐Bis(dimethylamino)naphthalene‐1,8‐dicarbaldehyde as “Push–Pull” Proton Sponges: When and Why Formyl Groups Become Stronger π‐Electron Acceptors than Nitro Groups

“…[21] Dipropylamino derivative 5 was obtained as dark orange needles in 19 % yield starting from 1,8-bis(dipropylamino)naphthalene [35] following the procedure described for preparation of its ethyl analogue 4; [21] Theoretical Calculations: DFT calculations were carried out by the restricted Hartree-Fock method with the Gaussian 98 program suite [36] at the B3LYP/6-31G** level of theory.…”

1,8-Bis(bromomethyl)naphthalene in the synthesis of 1,5-diazacyclodecane and benz[de]isoquinoline proton sponges

“…The reaction seems to proceed in three successive S N processes involving intermediates 12-14 and is reminiscent of the proton sponge realkylation reported by us earlier. 10 Undoubtedly, a key stage here is the nucleophilic attack of bromide onto the Me group in 12, which is facilitated by acidic catalysis through the formation of hydrogen bond, while the overall process is regulated by entropy factors favoring cyclization to the six-membered ring rather than the ten-membered as it would be in 9. …”

A method for determination of the structure of the intramolecular hydrogen bond in the cations of unsymmetrically substituted 1,8-bis(dimethylamino)naphthalenes in solution

“…To do this, diamine 5 was monodealkylated; the structures of the resulting nitro derivatives 6 and 7 were determined by X ray diffraction analysis (see Ref. 13). Since nitro naphthalene 6 proved to be inert toward MeI in the pres ence of KOH in both acetone and DMSO, subsequent experiments were carried out with its reactive and more accessible isomer 7.…”