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A facile, general route to adamantanophanes. Synthesis and conformational behavior of [4.4](1,3)Adamantanophan-trans,trans-1,8-diene (CROSBI ID 77558)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Mlinarić-Majerski, Kata ; Pavlović, Dražen ; Marinić, Željko A facile, general route to adamantanophanes. Synthesis and conformational behavior of [4.4](1,3)Adamantanophan-trans,trans-1,8-diene // Tetrahedron letters, 37 (1996), 28; 4829-4832. doi: 10.1016/0040-4039(96)00523-0

Podaci o odgovornosti

Mlinarić-Majerski, Kata ; Pavlović, Dražen ; Marinić, Željko

engleski

A facile, general route to adamantanophanes. Synthesis and conformational behavior of [4.4](1,3)Adamantanophan-trans,trans-1,8-diene

Ramber-Backlund rearrangement of disulfone 2 leads to the ring-contracted 4, 6:11, 13-di(1, 3-adamantano)cyclotetradeca-trans, trans-1, 8-diene (3a) along with 4, 6:11, 13-di(1, 3-adamantano)cyclotetradeca-cis, trans-1, 8-diene (3b! ) and 4, 6:12, 14-di(1, 3-adamantano)-8, 10-dehydro-9, 9-dichlorocyclopentadeca-1-diene (4) as a minor products. The ring inversion of 3a can most reasonably be interpreted in terms of equilibrium process between two conformers with effective C-2h symmetry.

Ramber-Backlund rearrangement ; [m.n]adamantanophanes ; dynamic NMR spectroscopy

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Podaci o izdanju

37 (28)

1996.

4829-4832

objavljeno

0040-4039

10.1016/0040-4039(96)00523-0

Povezanost rada

Kemija

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