Conformational Analysis of 3,4-Dihydropyridine and its Alkyl Derivatives
Russian Chemical Bulletin
The geometry of dihydropyridine and its alkyl derivatives was studied by the molecular mechanics method. The dihydrocycle was found to be mobile; however, substituents exert little effect on its distorted sofa conformation. The alkyl groups attached to the saturated carbon atoms occupy pseudo-equatorial position in monosubstituted and pseudo-axial positions in disubstituted 3,4-dihydropyridines. Unusually high barriers to inversion of the dihydrocycle were observed incis-3,4-dialkyl-3,4-dihydropyridines caused by the eclipse of the substituents in the transition state.
Shishkin, O. V.; Polyakova, A. S.; Desenko, S. M.; Orlov, V. D.; Lindeman, Sergey; and Struchkov, Yu T., "Conformational Analysis of 3,4-Dihydropyridine and its Alkyl Derivatives" (1994). Chemistry Faculty Research and Publications. 668.