caa a22 4500 475759702 CHVBK 20180406123547.0 cr unu---uuuuu 170329e20000701xx s 000 0 eng 10.1007/BF02495764 doi (NATIONALLICENCE)springer-10.1007/BF02495764 Rearrangement products of some 1 R ,4 R -2-arylidene- p -menthan-3-ones in acidic media, their structures, and conformational analysis [Elektronische Daten] [V. Vashchenko, N. Pivnenko, L. Kutulya, A. Petrenko, S. Iksanova, J. Goodby] 1R,4R-2-(4-Phenylbenzylidene)-p-menthan-3-one in acidic media undergoes rearrangement with migration of the exocyclic double bond to the cyclohexane ring to form three 2-(4-phenylbenzyl) derivatives ofp-menthen-3-ones. The reaction products differ in the location of the endocyclic double bond (Δ1 or Δ4) and in the configuration of the new chiral C(2) center in the resultingp-menth-4-en-3-ones. The configurations of the 1R,2R- and 1R,2S-2-(4-phenylbenzyl)-p-menth-4-en-3-ones were established based on analysis of their1H NMR spectra in combination with calculations by molecular mechanics. The molecular conformations of these compounds as well as of some racemic 2-benzyl-p-menth-1-en-3-one derivatives were studied. Kluwer Academic/Plenum Publishers, 2000 1 R ,4 R -2-(4-phenylbenzylidene)- p -menthan-3-one nationallicence rearrangement nationallicence isomeric 2-(4-phenylbenzyl)- p -menthen-3-ones nationallicence IR spectra nationallicence 1H NMR spectra nationallicence conformational analysis nationallicence molecular mechanics nationallicence Vashchenko V. Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001, Kharkov, Ukraine aut Pivnenko N. Kharkov State University, 4 pl. Svobody, 310077, Kharkov, Ukraine aut Kutulya L. Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001, Kharkov, Ukraine aut Petrenko A. Department of Chemistry, University of Hull, HU6 7RX, Hull, UK aut Iksanova S. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 ul. Murmanskaya, 252660, Kiev, Ukraine aut Goodby J. Department of Chemistry, University of Hull, HU6 7RX, Hull, UK aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1218-1230 1066-5285 49:7<1218 2000 49 11172 https://doi.org/10.1007/BF02495764 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495764 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Vashchenko V. Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001, Kharkov, Ukraine aut NATIONALLICENCE 700 1- Pivnenko N. Kharkov State University, 4 pl. Svobody, 310077, Kharkov, Ukraine aut NATIONALLICENCE 700 1- Kutulya L. Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 310001, Kharkov, Ukraine aut NATIONALLICENCE 700 1- Petrenko A. Department of Chemistry, University of Hull, HU6 7RX, Hull, UK aut NATIONALLICENCE 700 1- Iksanova S. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 ul. Murmanskaya, 252660, Kiev, Ukraine aut NATIONALLICENCE 700 1- Goodby J. Department of Chemistry, University of Hull, HU6 7RX, Hull, UK aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1218-1230 1066-5285 49:7<1218 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer