70188-06-6

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 112238-64-9 phenylselenyl triflate 
• 34837-55-3 Phenylselenyl bromide 

Relevant academic research and scientific papers

Cyclization of some terpenic alcohols by phenylselenoetherification reaction

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.

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

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

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.

The Use of Acyclic Monoterpenes in the Preparation of β-pyrones; Synthesis of the Right-hand Fragment of Usneoidone E

The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the β-pyrone 32.Using lanalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized from geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetraprenyltoluquinols.Unambiguous 13C NMR assignment has been done by 2D correlations.

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

Cyclization of terpene alcohols and related polyenols by benzeneselenenyl triflate

Electrophilic cyclization of dienols and trienols, such as homogeraniol, homonerol, and farnesol, by benzeneselenenyl triflate proceeds with carbon-carbon bond formation to afford mono-, di-, and tricyclic compounds.