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NMR-Spectroscopic, computational and mass-spectrometric investigations on the cis / trans analogues of 2,3,4-trihydronaphthalene-1-one

Tetrahedron, ISSN: 0040-4020, Vol: 59, Issue: 8, Page: 1309-1316
2003
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NMR-Spectroscopic, computational and mass-spectrometric studies of the cis / trans isomers of N -[8-(acetylamino)-4-(2,2-dimethyl-1,1-diphenyl-silapropoxy)-6-fluoro-5-methyl-1-one-2,3,4-trihydronaphthyl]acetamide ( 1a and 1b ), obtained as intermediates in the synthesis of an important class of alkaloid molecules, are reported. 1 H and 13 C NMR analyses show an unusual axial preference of the TBDPSi– ( tert -butyldiphenylsilyl) group in position 4 in both the isomers. Mass spectrometric evidence demonstrates that trans isomer has a higher affinity for ammonium ions than the cis isomer and that only the ammonium adduct [ 1b +NH 4 ] + and the protonated molecule [ 1b +H] + show the fragmentation in which loss of benzene is observed. Moreover, molecular mechanics and semi-empirical calculations indicate that a group of trans conformers tend to place one of the phenyl rings of the TBDPSiO– group in a offset π-stacked geometry with the compound's aromatic ring. The combination and the detailed analyses of these experimental and theoretical results could support the π–π interaction obtained as a conformational preference in the trans isomer.

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