200068-17-3

Upstream product

• 144427-99-6 1-(2-iodophenyl)-1-methyloxirane 
• 77129-69-2 dibutyl ditelluride 

Relevant academic research and scientific papers

Intramolecular homolytic substitution at tellurium: Preparation of a dihydrotellurophene by alkyltelluride-mediated S(RN)1/S(H)i reactions

Reaction of 1-methyl-1-(2-iodophenyl)oxirane (4) with two equivalents of sodium butyltelluroate (NaTeBu), generated throught the sodium borohydride reduction of dibutylditelluride, in THF, affords 2,3-dihydro-3-hydroxy-3- methylbenzo[b]tellurophene (6) in

Toward Novel Antioxidants: Preparation of Dihydrotellurophenes and Selenophenes by Alkyltelluride-Mediated Tandem SRN1/SHi Reactions

Reaction of 1-(2-iodophenyl)-1-methyloxirane (12) with 2 equiv of sodium n-butyltellurolate (n-BuTeNa), generated by the sodium borohydride reduction of di-n-butyl ditelluride, in THF, affords 2,3-dihydro-3-hydroxy-3-methylbenzo[b]tellurophene (13) in 62% yield, together with a small quantity of 1-(n-butyltelluro)-2-phenyl-2-propanol (27). This transformation presumably involves a tandem SRN1/SHi sequence. Similar reactions of 1-(benzylseleno)-2-phenyl-2-propanol (5a, R = Me) and 1-allyloxy-2-iodobenzene (15) afforded 2,3-dihydro-3-hydroxy-3-methylbenzo[b]selenophene (17, 74%), and 3-(n-butyltelluro)methyl-2,3-dihydrobenzo[b]furan (18, 50%), respectively. Lithium alkyltellurolates, generated by direct tellurium insertion into the required alkyllithium, or sec-butyl or tert-butyl substitution on tellurium provide product distributions similar to those observed for reactions involving n-BuTeNa. Lithium or sodium phenyltellurolate returned only starting materials from these reaction mixtures. The 2-[2-(n-butyltelluro)-1-hydroxy-1-methyl]ethylphenyl radical (14) is estimated to cyclize with kc 5 × 108 s-1 at 25 °C. The tandem SRN1/SHi sequence has been applied to the preparation of the antioxidant analogues, 5-hydroxy-2,3-dihydrobenzo[b]- tellurophene and selenophene (31, 32).