NMR investigation of adamantane derivatives of
1,3-; 1,4-; 2,6- и 2,7-dihydroxynaphthalenes.
I.V. Peterson,1 N .M. Svirskaya1, A.A Kondrasenko1 and A.I. Rubaylo1, 2, 3
1
Institute of chemistry and chemical technology SB RAS,
660036, Russia, Krasnoyarsk, Akademgorodok 50, bld.24.
2
Krasnoyarsk scientific centre SB RAS, 660036, Russia, Krasnoyarsk, Akademgorodok 50.
3
Siberian federal university, 660041, Russia, Krasnoyarsk, Svobodniy av. 79.
E-mail: Ivan.Peterson.Krsk@gmail.com
A great number of the adamantane derivatives have shown many possibilities of practical
application[1]. The interaction of dihydroxynaphthalenes with adamantane has not been previously
investigated systematically. Thereby, there is no information about the structural features of
adamantane derivatives of different dihydroxynaphthalenes. Moreover, recently much attention has
been heeded to dearomatization reactions of aromatic compounds due to the highly reactive
intermediates opportunities [2].
Current report is our ongoing research of determination structure of adamantyl derivatives of
dihydroxynaphthalenes by NMR spectroscopy
[3,4]
. We describe here assignments and spectral
features of 1H and 13C NMR spectra of synthesized 1-adamantyl substituted 1,3- (I); 1,4- (II); 2,6(III) and 2,7- (IV) dihydroxynaphthalenes (Scheme 1).
H
OH
H
O
OH
O
1-AdOH
1-AdOH
CF3COOH:CDCl3
in NMR tube
I
H
OH
H
CH3COOH:
H3PO4
H
H
H
O
II OH
OH
1-AdOH
HO
III
different
acid media
Ad
All NMR spectra (1H,
Ad
CD2Cl2
inert atmoshere under
argon in sealed NMR tube
Ad
+O2
-H2O
Ad=
O
OH
1-AdOH
different
acid media
IV
X
Ad
OH
HO
H
O
Ad
morpholine
OH
HO
OH
H
OH
Ad
1-AdOH
CF3COOH
H
CF3COOH:CDCl3
in NMR tube
O
Ad
O
OH
O
H
HO
OH
Ad
Ad
C, COSY, NOESY, HSQC, HMBC) were collected on a “Bruker
13
Avance III 600” spectrometer system (14.1 T, Krasnoyarsk centre of shared using SB RAS).
Reference
[1] H. Schwertfeger, A. F. Fokin, P. R. Schreiner. Angew. Chem. Int. Ed., 2008, 47, 1022–1036.
[2] M. A. Schätzle, S. Flemming, S. M. Husain, S. Günther, M. Müller. Angew. Chem. Int. Ed., 2012, 51, 2643–2646.
[3] I. V. Peterson, N. M. Svirskaya, A. A. Kondrasenko, A. I. Rubaylo. Magn. Reson. Chem., 2013, 51, 762–766.
[4] I. V. Peterson, N. M. Svirskaya, A. A. Kondrasenko, A. I. Rubaylo. Magn. Reson. Chem., 2015, 53, in print.