120596-69-2

Upstream product

• 628-21-7 1,4-Diiodobutane 
• 1666-13-3 diphenyl diselenide 
• 182635-00-3 1-chloro-4-(phenylselanyl)butane 
• 1132-39-4 diphenylselenide 

Downstream Products

• 182635-01-4 2-Allyl-2-(4-phenylselanyl-butyl)-malonic acid diethyl ester 
• 191542-44-6 1-<4-(phenylselanyl)butyl>-2-(phenylsulfanyl)-1H-benzimidazole 
• 191542-41-3 1-<4-(phenylselanyl)butyl>-2-tosyl-1H-imidazole 
• 895581-99-4 2-chloro-1-[(4-phenylselanyl)butyl]-1H-benzo[d]imidazole 
• 941306-82-7 4,7-dimethoxy-1-[4-(phenylseleno)butyl]-1H-benzimidazole 
• 941306-85-0 5,6-dimethyl-1-[4-(phenylseleno)butyl]-1H-benzimidazole 
• 457925-31-4 4-phenyl-1-[4-(phenylselanyl)butyl]-1H-pyrazole 
• 1052104-58-1 2-methyl-1-[4-(phenylselanyl)butyl]-1H-imidazole 
• 182635-05-8 2-Allyl-6-phenylselanyl-hexanoic acid ethyl ester 
• 171190-55-9 6-benzeneselenyl-2-(2-propen-1-yl)hexanal 
• 895582-02-2 4-({1-[(4-phenylselanyl)butyl]-1H-benzo[d]imidazol-2-yl}sulfanyl)benzoic acid 

Relevant academic research and scientific papers

Radical cyclisation onto imidazoles and benzimidazoles

New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.

Cascade radical cyclisations of imines

Cascade radical reactions, initiated by cyclisation of sp3 carbon-centred radicals onto the C-atom of imines, have been used to develop a new protocol for the synthesis of a range of nitrogen heterocycles. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH. The aminyl radicals generated by cyclisation onto imines undergo further 5- or 6-exo cyclisation with suitably placed alkenes.

CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES

A free radical mediated ring expansion of cis- and trans-α-alkylated-β-stannylcyclohexanones to provide efficient routes to cis- and trans-cyclononenones and cyclodecenones is described.The cis-/trans- relationship in the precursor was found to have signi