92691-96-8Relevant academic research and scientific papers
A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids
Kosti?, Marina,Verdía, Pedro,Fernández-Stefanuto, Verónica,Puchta, Ralph,Tojo, Emilia
supporting information, (2019/01/08)
A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with ab
Cyclization of some terpenic alcohols by phenylselenoetherification reaction
Rvovic, Marina D.,Divac, Vera M.,Jankovic, Nenad Z.,Bugarcic, Zorica M.
supporting information, p. 1227 - 1231 (2013/08/23)
Highly substituted tetrahydrofuran (THF)- and tetrahydropyran (THP)-type rings are formed through an acid- or base-catalyzed 5-exo and/or 6-endo cyclization of some natural terpenic alcohols (e.g., linalool, nerolidol, and α-terpineol) by an electrophile-mediated cyclization with PhSeCl and PhSeBr. The side chains of these cyclic ether products can be further transformed easily into a wide range of substrates owing to the versatile functionality of the double bond. Certain regioselectivity was noticed in these reactions. Nerolidol behaves like linalool in the reaction with PhSeX and affords predominantly THF derivatives, whereas α-terpineol affords THPs. Some Lewis bases (triethylamine, pyridine, 2,2′-bipyridine, and quinoline) and Lewis acids (SnCl2 and CoCl2) were used as additives, the presence of which increases the yields from 5-40 % to almost quantitative.
A simple, convenient and expeditious approach to cineol
Bugar?i?, Zorica M.,Dunki?, Jelena D.,Mojsilovi?, Biljana M.
, p. 468 - 470 (2007/10/03)
A convenient two-step protocol preparation of cineol (1-isopropyl-4-methyl- 7-oxabicyclo-[2,2,1]heptane) from α-terpineol (p-menth-1-en-8-ol) is reported. The phenylselenoetherification of α-terpineol with PhSeX (X = Cl, Br, I) as a key step is described. α-Terpineol reacts with PhSeX to form the corresponding phenylselenoether in short reaction time and in quantitative yield. A subsequent reduction with Bu3SnH to cineol proceeds in high yield (98%)
9,10-Dihydroxy-1,8-cineole (1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane-10,11-diol)
Carman, Raymond M.,Handley, Paul N.
, p. 769 - 776 (2007/10/03)
The title compound (3) has been synthesized and its presence sought in the urinary metabolites of the brushtail possum.
SYNTHESIS OF DEHYDROCINEOLE, A NEW MONOTERPENE FROM THE ACARID MITE, Caloglyphus rodriguezi (ARACHNIDA: ACARI)
Ayorinde, F. O.,Wheeler, J. W.,Duffield, R. M.
, p. 3525 - 3528 (2007/10/02)
Dehydrocineole, a new monoterpene ether, 6-methylsalicylaldehyde, undecane and tridecane are reported from the opisthonotal gland secretion of the mite, Caloglyphus rodriguezi.A synthesis of dehydrocineole is described.
