Phenylselenoetherification of some Δ4-alkenols facilitated by pyridine and some Lewis acids
Studies on the phenylselenoetherification of some Δ4- alkenols in the presence of pyridine and some Lewis acids are described. All alkenols underwent intramolecular cyclization yielding corresponding tetrahydrofuran or tetrahydropyran derivativ
S, Biljana M.,Bugarcic, Zorica M.
experimental part
p. 1443 - 1446
(2011/03/17)
Pyridine-facilitated phenylselenoetherification of some tertiary alkenols
An improved procedure for intramolecular cyclization of tertiary alkenols using benzeneselenyl halides has been developed. We found that cyclization can be facilitated by pyridine. Thus, in the presence of an equimolar amount of pyridine, a chemospecific
Mojsilovic, Biljana M.,Bugarcic, Zorica M.
p. 475 - 479
(2007/10/03)
Simple synthesis of karahanaenone
Karahanaenone 1 has been prepared from linalool 3. Linalool 3 is cyclized to the corresponding tetrahydrofuran-type cyclic ethers 4a-c on treatment with PhSeCl, N-bromosuccinimide, and 3-chloroperbenzoic acid, respectively. 4a-c on further treatment with various reagents, provide allylic cyclic ether 6 which is converted to 1 via 2.
Konstantinovic, S.,Bugarcic, Z.,Marjanovic, Lj.,Gojkovic, S.,Mihailovic, M. Lj.
p. 1169 - 1170
(2007/10/03)
Regioselectivity in Cyclofunctionalization of Olefinic Alcohols with Benzeneselenenyl Halides at Different Temperatures
The regioselectivity in cyclofunctionalization of some acyclic olefinic alcohols with benzeneselenenyl halides (PhSeCl and PhSeBr) at different temperatures (-78 deg C, 0 deg C and room temperature) is investigated.It has been found that Δ4- and Δ5-alkenols are converted into five- and/or six-membered cyclic phenyl selenoethers, the yield of which decreases with increasing temperature.PhSeCl has been found to be more efficient than PhSeBr in the cyclization reactions. Key Words: Olefinic alcohols / Cyclofunctionalization / Benzeneselenenyl halides