527-83-3Relevant articles and documents
STUDIES OF COMPOUNDS IN THE MENTHANE SERIES. XIX. SYNTHESIS AND PROPERTIES OF TRANS-o-4-MENTHEN-8-OL AND STEREOISOMERIC o-5-METHEN-8-OLS
Bazyl'chik, V. V.,Fedorov, P. I.,Klyuev, N. A.,Dank, E. Kh.
, p. 1320 - 1327 (2007/10/02)
Trans-o-4-Menthen-8-ol and cis- and trans-o-5-menthen-8-ols have been prepared via the Diels-Alder reactions of 1,3-butadiene with crotonaldehyde in the presence of boron trifluoride etherate, and piperylene with methyl acrylate, respectively.The dehydration reactions of these alcohols have been studied in the presence of acetic anhydride and potassium bisulfate; the latter reagent demonstrates a high reaction selectivity.
STUDIES OF COMPOUNDS IN THE MENTHANE SERIES. XVIII. VAPOR PHASE ISOMERIZATION OF o-1,4-MENTHADIENE IN THE PRESENCE OF DIATOMACEOUS EARTH
Bazyl'chik, V.V.,Fedorov, P.I.,Skakovskii, E.D.,Klyuev, N.A.
, p. 1316 - 1319 (2007/10/02)
Vapor phase isomerization of o-1,4-menthadiene in the presence of diatomaceous earth results in deprotonation of the 1,2 and 4,5 positions to give an equilibrium mixture of o-menthadienes containing both endo- and exocyclic double bonds; the skeletal rearrangement products, 2-isopropyl-3-ethylidene-1-cyclopentene and 4-isopropyl-3-ethylidene-1-cyclopentene, are also formed. o-Menthadienes also undergo dehydrogenation to give o-cumene, and disproportionation to give a mixture of o-cumene and o-menthenes.The dehydrogenation process predominates as the temperature is increased.
INVESTIGATION OF COMPOUNDS IN THE o-MENTHANE SERIES XI. ISOMERIZATION TRANSFORMATIONS OF o-1,4-MENTHADIENES
Bazyl'chik, V. V.,Fedorov, P. I.
, p. 1221 - 1227 (2007/10/02)
Under the conditions of base catalysis under the influence of potassium tert-butoxide in dimethyl sulfoxide and lithium and calcium amides o-1,4-menthadiene forms equilibrium mixtures of o-1,3-menthadiene, o-1,5-menthadiene, and the skeletal rearrangement product 1-isopropyl-5-ethylidenecyclopentene.In the presence of NaX and KX zeolites competing dehydrogenation and disproportionation of the hydrogen occur in o-1,4-menthadiene with the formation of a mixture of o-menthenes and o-cymene.With increase in temperature the dehydration process becomes determining.With acid catalysis the transformation of o-1,4-menthadiene into 1-isopropyl-5-ethylidenecyclopentene and dehydration to o-cymene are the mainpaths.