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eral formula C11H17NO. GC–MS data: 19.7 min (25%),
mass spectrum, m/z (Irel, %): 179 (90) [M]+, 164 (96)
[M – CH3]+, 136 (52) [M – CH3CO]+, 120 (58), 105
(37); 19.9 min (75%), mass spectrum, m/z (Irel, %): 193
(14) [M]+, 164 (28) [M – CH3]+, 136 (57) [M –
CH3CO]+, 120 (100). The oxidation of 2,4-dehydro-
adamantane (V) gave a complex mixture of products,
among which we identified monoacetamides with the
general formula C12H19NO: 21.2–21.4 min (38%),
mass spectrum, m/z (Irel, %): 193 (100) [M]+, 178 (24)
[M – CH3]+, 150 (31) [M – CH3CO]+, 134 (56) [M –
CH3CONH2]+, 119 (14), 92 (70); and bis-acetamides
C14H22N2O2: 24.1 min (5%), mass spectrum, m/z
(Irel, %): 207 (44) [M – CH3CO]+, 179 (100), 164 (31)
[M – 2CH3CO]+, 136 (26), 120 (48).
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Quantum-chemical calculations were performed
using Gaussian09 [37] and Gaussian03 software
packages [38] supplemented by the Grimme dispersion
corrections.* All optimized structures occupied mini-
ma on the potential energy surface, as followed from
the calculation of their normal vibration frequencies
(Nimag = 0). The calculated relative electronic energies
were neither corrected nor scaled.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 9 2011