Center for Magnetic Resonance

A.E. Kulyashova, E.V. Mikheeva, N.A. Danilkina, I.A. Balova
“Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines using reductive methylation step”

Mendeleev Commun., 2014, 24, 102-104

DOI: 10.1016/j.mencom.2014.03.013

Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines based on reductive methylation of ortho-iodoanilines using CH2O–NaBH3CN and coupling with terminal diacetylens was developed. Altered sequence including dimethylation of 2-(buta-1,3-diynyl)anilines was also successfully achieved and gave higher overall yields in the case of anilines without acceptor substituent in the ring.

A. Penkova, G. Polotskaya, A. Toikka
“Pervaporation composite membranes for ethyl acetate production”
Chem. Eng. Process., 2014, accepted
DOI: 10.1016/j.cep.2014.11.015

T. Minh Dau, Y.-A. Chen, A.J. Karttunen, E.V. Grachova, S.P. Tunik, K.-T. Lin, W.-Y. Hung, P.-T. Chou, T.A. Pakkanen, I.O. Koshevoy
“Tetragold(I) complexes: solution isomerization and tunable solid-state luminescence”
Inorg. Chem., 2014, accepted

A.I. Solomatina, D.V. Krupenya, V.V. Gurzhiy, I. Zlatkin, A.P. Pushkarev, M.N. Bochkarev, N.A. Besley, E. Bichoutskaia, S.P. Tunik
“Cyclometallated platinum(II) complexes containing NHC ligands; synthesis, characterization, photophysics and their application as emitters in OLEDs”
Dalton Trans., 2014, accepted

First paper of 2015 with acknowledgments to CMR:

M.Ya. Demakova, D.S. Bolotin, N.A. Bokach, G.L. Starova, V.Yu. Kukushkin

“Metal-mediated cyanamide–hydroxyguanidine coupling” Inorg Chim. Acta, 2015, 425, 114-117

DOI: 10.1016/j.ica.2014.10.015

Reaction of the cyanamides R₂NCN (R = Me 2a, Et 2b) with the hydroxyguanidine OC₄H₈NC(=NOH)NH₂ (1) in the presence of zinc halides leads to [ZnX₂{HN=C(NR₂)ON=C(NH₂)NC₄H₈O}] derived from the ZnIImediated cyanamide–hydroxyguanidine coupling. This reaction is the first observation of interplay between any nitrile group and any hydroxyguanidine both in metal-involving and metal-free chemistry. Complexes 3a,b–5a,b rather rapidly degrade in solutions at RT, but solvates 3a,b MeOH and 4a MeOH are sufficiently stable in the solid state and they were characterized by IR, HRESI⁺-MS, solid state CP-MAS TOSS ¹³C NMR, and X-ray crystallography (for 3a,b). Complexes 4b and 5a,b were identified in solutions by HRESI⁺-MS.

A.S. Konev, A.F. Khlebnikov, P.I. Prolubnikov, A.S. Mereshchenko, A.V. Povolotskiy, O.V. Levin, A. Hirsch, “Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge-Separated States on a Microsecond Lifetime Scale”
Chem. Eur. J. 2014, 20, 1-15
DOI: 10.1002/chem.201404435

N.A. Danilkina, A.E. Kulyashova, A.F. Khlebnikov, S. Bräse, I.A. Balova, “Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core”
J. Org. Chem. 2014, 79(19), 9018-9045
DOI: 10.1021/jo501396s

A.F. Khlebnikov, O.A. Tomashenko, L.D. Funt, M.S. Novikov, “Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides”
Org. Biomol. Chem. 2014, 12, 6598-6609
DOI: 10.1039/c4ob00865k

A.S. Konev, D.A. Lukyanov, P.S. Vlasov, O.V. Levin, A.A. Virtsev, I.M. Kislyakov, A.F. Khlebnikov, “The Implication of 1,3-Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main-Chain Porphyrin Oligomers”
Macromol. Chem. Phys. 2014, 215, 516-529
DOI: 10.1002/macp.201300679

P.V. Gushchin, M.L. Kuznetsov, M. Haukka, V.Yu. Kukushkin, “Anionic halide…alcohol clusters in the solid state”
J. Phys. Chem. A 2014, 118,, 9529-9539
DOI: 10.1021/jp506256a

A.F. Khlebnikov, M.S. Novikov, Y.G. Gorbunova, E.E. Galenko, K.I. Mikhailov, V.V. Pakalnis, M.S. Avdontceva “Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines”
Beilstein J. Org. Chem. 2014, 10, 1896-1905
DOI: 0.3762/bjoc.10.197

K.V. Zavyalov, M.S. Novikov, A.F. Khlebnikov, V.V. Pakalnis, “Selective syntheses of 2H-1,3-oxazines and 1H-pyrrol-3(2H)-ones via temperature-dependent Rh(II)-carbenoid-mediated 2H-azirine ring expansion”
Tetrahedron 2014 2014, 70(21), 3377-3384
DOI: 10.1002/macp.201300679

A.N. Kazakova, R.O. Iakovenko, V.M. Muzalevskiy, I.A. Boyarskaya, M.S. Avdontceva, G.L. Starova, A.V. Vasilyev, V.G. Nenajdenko
“Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’”

Tetrahedron Lett., 2014, 55, 6851-6855

DOI: 10.1016/j.tetlet.2014.10.083

An unusual ‘dimerization’ of CF₃-allyl alcohols [ArCH=CHCH(OH)CF₃] under the action of anhydrous FeCl₃ was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF₃-allyl alcohols with arenes (Ar′H) led to CF₃-alkenes [Ar(Ar′)CHCH=CHCF₃] in 48–75% yields. The mechanisms of the transformations are discussed.