Reaction of Tetraorganyltelluriums with Acetylenes

Li Biao Han, Nobuaki Kambe*, Akiya Ogawa, Ilhyong Ryu, Noboru Sonoda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Tetraalkyltelluriums (R4Te) react with arylacetylenes (ArCCH; Ar = Ph, p-MeOC6H4, p-FCeH4) to afford alkylation products (ArHCCHR). The alkylation proceeds preferentially in net trans fashion to give a cis-1,2-disubstituted olefin as the major product along with the concomitant formation of a tellur ide (R2Te) and an alkene originated from a substituent of R4Te which plays as a hydrogen source. The reaction of dibutyldidecyltellurium (nBu2TenDec2) with phenylacetylene yields nearly statistical ratios of products, PhCHCHnBu (41%, E/Z = 10/90), PhCHCHnDec (35%, E/Z = 11/89), nBu2Te (20%), nBuTenDec (41%), and nDec2Te (18%), indicating a random transfer of primary alkyl substituents. On the contrary, nBu2TeiPr2 reacts with phenylacetylene much faster than nBu4Te affording only PhCHCHiPr. Under similar conditions Ph4Te does not react with phenylacetylene and nDec2TePh2 decomposes quickly to nDecTePh (95%), 1-decene (93%), and benzene (99%). The alkylation is proposed to proceed by the radical addition of R4Te to ArCCH to yield (R3Te) ArCCHR, which then decomposes to afford an olefin via a β-hydrogen transfer from R on tellurium to the vinyl carbon.

Original languageEnglish
Pages (from-to)473-477
Number of pages5
JournalOrganometallics
Volume12
Issue number2
DOIs
StatePublished - 1 Jan 1993

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