TY - JOUR
T1 - Proton-induced supramolecular dimerization of aminomethylbenzo-15-crown-5 accompanied by a covalent dimerization of cyanoborohydride anion
AU - Kryatova, Olga P.
AU - Korendovych, Ivan V.
AU - Rybak-Akimova, Elena V.
N1 - Funding Information:
We thank the NSF and Tufts University (FRAC) for funding, and Mr. V. Azev for helpful discussions. The X-ray facility at Tufts was supported by AirForce DURIP grant F49620-01-1-0242.
PY - 2003/5/26
Y1 - 2003/5/26
N2 - Reductive amination of 4′-formyl[benzo-15-crown-5] with sodium cyanoborohydride in the NH4Ac/MeOH medium followed by acid addition and extraction with CHCl3 unexpectedly lead to the isolation of the salt (B15C5-CH2-NH3)+-(H 3BCNBH2CN)- with an unusual dicyanodiborohydride anion. The self-complementary 4′-ammoniomethyl[benzo-15-crown-5] cation was found to exist as a supramolecular dimer in the solid state, acetonitrile solution, and gas phase as revealed by X-ray crystallography, NMR and mass spectrometry, respectively.
AB - Reductive amination of 4′-formyl[benzo-15-crown-5] with sodium cyanoborohydride in the NH4Ac/MeOH medium followed by acid addition and extraction with CHCl3 unexpectedly lead to the isolation of the salt (B15C5-CH2-NH3)+-(H 3BCNBH2CN)- with an unusual dicyanodiborohydride anion. The self-complementary 4′-ammoniomethyl[benzo-15-crown-5] cation was found to exist as a supramolecular dimer in the solid state, acetonitrile solution, and gas phase as revealed by X-ray crystallography, NMR and mass spectrometry, respectively.
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U2 - 10.1016/S0040-4039(03)00894-3
DO - 10.1016/S0040-4039(03)00894-3
M3 - Article
AN - SCOPUS:0038739162
SN - 0040-4039
VL - 44
SP - 4251
EP - 4255
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 22
ER -