70813-85-3

Upstream product

• 645-96-5 Benzeneselenol 
• 156-87-6 propan-1-ol-3-amine 
• 503-30-0 trimethylene oxide 
• 1666-13-3 diphenyl diselenide 
• 627-18-9 1-bromo-3-propanol 
• 627-32-7 1-iodopropan-3-ol 

Downstream Products

• 118824-31-0 1-bromo-3-phenylselenopropane 
• 118824-30-9 3-(3-phenylselenopropanoxy)cyclohex-2-en-1-one 
• 184781-47-3 [3-(2-Methyl-1-nitromethyl-propoxy)-propylselanyl]-benzene 
• 128813-58-1 6-(but-3-enyl)-3-(3-phenylselenopropanoxy)cyclohex-2-en-1-one 
• 118824-29-6 3-(3-phenylselenopropanoxy)-2-methylcyclopent-2-en-1-one 

Relevant academic research and scientific papers

α-Alkylation of tertiary amines by C(sp3)–C(sp3) cross-coupling under redox neutral photocatalysis

Direct α-alkylation of N-phenyl-tetrahydroisoquinoline with alkyl selenides of desired alkyl chain length and functionality is reported by photoredox catalysis. Construction of hexahydro pyrrolo- and pyrido-isoquinoline scaffolds along with indolines and tetrahydroquinolines is also described by intramolecular C(sp3)–C(sp3) cross-couplings.

Reactivity of chlorooxachalcogenuranes: Oxidation of sulfides to sulfoxides using chlorooxaselenuranes

The transformation of chloro between chlorooxachalcogenuranes 3 and chalcogenides 4 is described. The oxidative ability of chlorooxachalcogenuranes has been compared. Selenuranes 3a, b have been found to be good reagents for selective oxidation of sulfide

Synthesis of cyclic halooxatelluranes via dehalogenation of α-halo carbonyl compounds with tellurides containing hydroxy group on side chain

The synthesis of cyclic halooxatelluranes (3a, 4a-d, 5a) has been achieved via dehalogenation of α-halo carbonyl compounds (2A-F) with tellurides(1a-d) containing hydroxy group on the side chain. Halophilicity of the tellurides was compared with that of selenides and a plausible reaction mechanism is discussed.

Solid-phase combinatorial synthesis of polyisoxazolines: A two-reaction iterative protocol

Starting from a polymer-bound olefin, iterative application of nitrile oxide 1,3-dipolar cycloaddition and selenide oxidation/elimination steps were employed to deliver a polymer-bound triisoxazoline that can be liberated from the resin by transesterification. When four nitroseleno ethers (2-5) and four capping nitroalkanes (6-9) were employed, a triisoxazoline library (V) of 64 positional isomers was obtained by three iterative applications of these two reactions. The tactical flexibility of this strategy for preparing small polyfunctional oligomers is particularly attractive in that each subunit addition proceeds via a C-C bond-forming step.

Intramolecular SH2 macrocyclisations

The synthesis of 10-15 membered α-methylene macrocyclic lactones from the functionalised allylstannanes (7e)-(7j) is described. Attempts to synthesise analogous 6-9 membered lactones proved unsuccessful, resulting instead in the production of dilactones and AIBN derived adducts.

Radical Reactions in Synthesis: Intramolecular SH2' Macrocyclisations

The synthesis of 10-15 membered α-methylene lactones 1 from the functionalised allyl stannanes 2 occurs cleanly in moderate to high yield under free radical conditions via an intramolecular SH2' reaction.

SYNTHESIS OF SPIROETHERS USING RADICAL CYCLISATIONS

A variety of spiroether products, including one bis-spiro compound, are avaible via a simple radical cyclisation route.

Preparation of γ- and δ-Phenylselenyl Alcohols via Ring Cleavage of Oxetane and Oxolane

Various types of oxetanes and oxolanes can be cleaved by reaction with phenylselenide anion prepared from diphenyl diselenide and lithium aluminum hydride in dioxane.

Cleavage of Cyclic Ethers Including Oxetane and Oxolane with a Highly Nucleophilic Species of Phenylselenide Anion

Phenylselenide anion generated from (PhSe)2 and LiAlH4 was found to be highly reactive to various types of cyclic ethers, providing a new method to prepare γ- and δ-phenylselenenyl alcohols from oxetane and oxolane, respectively.