Naphthalene protonated

Cl3CCH20CH2Br, l,8-bis(dimethylamino)naphthalene (proton sponge), CH3CN, 0-25°, >87% yield. ... 

Exposure of naphthalene dissolved in liquid ammonia to europium metal immediately results in the characteristic green color of naphthalene anion-radical. ESR analysis reveals a signal that comes from an unpaired electron interacting with Eu and Eu nuclei. No hyperfine coupling with naphthalene protons is observed, although treatment with water leads to 1,4-dihydronaphthalene (Stevenson et al. 1999). This means that naphthalene has indeed been reduced to its anion-radical and undergone a normal Birch reaction. These results are consistent with the initial donation of two... 

The acylate anion from Mn(CO)3(j/-C5H5) and LiMe reacts similarly reaction with l,8-bis(dimethylamino)naphthalene (proton sponge) affords the vinylidene, although in this reaction, it is the binuclear complex which is isolated as the final product (38) ... 

Since the spin-spin relaxation of the liquid phase naphthalene protons is much longer than that of the solid naphthalene protons, by once more using the spin-echo sequence with x =. 007 s we are able to monitor the NMR signal from the liquid phase only. 

The Potential Energy Shape for the Proton Motion in Protonated Naphthalene Proton Sponges (DMAN-s) and its Manifestations... 

Abstract The problem of the low-barrier hydrogen bond in protonated naphthalene proton sponges is reviewed. Experimental data related to the infra-red and NMR spectra are presented, and the isotope effects are discussed. An unusual potential for the proton motion that leads to a reverse anharmonicity was shown The potential energy curve becomes much steeper than in the case of the harmonic potential. The isotopic ratio, i.e., vH/VD (v-stretching vibration frequency), reaches values above 2. The MP2 calculations reproduce the potential energy curve and the vibrational H/D levels quite well. A critical review of contemporary theoretical approaches to the barrier height for the proton transfer in the simplest homoconjugated ions is also presented. 

A.F. Pozharskii, Naphthalene proton sponges (naftalinovye protonnye gubki). Usp. Khim. 67,... 

Quite interestingly, the minor product 2-pheny 1-2,5-dihydrofuran (200) has the opposite configuration, i.e., (5)-200, compared to that of (/ )-199. However, this compound is produced with a significantly lower enantiomeric excess. It is possible that this is caused by a kinetic resolution effect in the alkene complex 205 the jr-bound hydridopalladium moiety in complex 205 could add again to the double bond. Base influence is also noteworthy, and the highest enantiomeric excess was achieved with l,8-bis(bisdimethylamino)naphthalene ( proton sponge ). 

C. Analogues of the Naphthalene Proton Sponge with A-Substituents... 

FIGURE 3. Various types of dimethylamino group conformations in naphthalene proton sponges (white rectangles denote the side view of the mean ring plane)... 

Selective displacement of one CIT3 by the CD3 group was employed to establish the structure of IF1B in the cations of non-symmetrically substituted naphthalene proton sponges by FI NMR1". This direct method is simple and does not require NMR on other nuclei such as deuterium, carbon or nitrogen. 

Reactivity features of double and 2,7-disubstituted naphthalene proton sponges... 

D. Transformations of Naphthylmethyl Carbocations Derived from Naphthalene Proton Sponges... 

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