INTRAMOLECULAR HOMOLYTIC SUBSTITUTION AT TELLURIUM - PREPARATION OF ADIHYDROTELLUROPHENE BY ALKYLTELLURIDE-MEDIATED S(RN)1 S(H)I REACTIONS/

Authors
LAWS MJ SCHIESSER CH
Citation
Mj. Laws et Ch. Schiesser, INTRAMOLECULAR HOMOLYTIC SUBSTITUTION AT TELLURIUM - PREPARATION OF ADIHYDROTELLUROPHENE BY ALKYLTELLURIDE-MEDIATED S(RN)1 S(H)I REACTIONS/, Tetrahedron letters, 38(48), 1997, pp. 8429-8432
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
48
Year of publication
1997
Pages
8429 - 8432
Database
ISI
SICI code
0040-4039(1997)38:48<8429:IHSAT->2.0.ZU;2-Q
Abstract
Reaction of 1-methyl-1-(2-iodophenyl)oxirane (4) with two equivalents of sodium butyltelluroate (NaTeBu), generated throught the sodium boro hydride reduction of dibutylditelluride, in THF, affords 2,3-dihydro-3 -hydroxy-3-methylbenzo[b]tellurophene (6) in 57% yield, together with 1-(butyltelluro)-2-phenyl-2-propanol (7, 7%). This transformation pres umably involves a tandem S(RN)1/S(H)i sequence which was investigated further through the reactions of 1-(benzylseleno)-2-phenyl-2-propanol (2, R-1 = Me; R-2 = H) and 1-allyloxy-2-iodobenzene (9) with sodium bu tyltelluroate under similar conditions. Mechanistic and kinetic implic ations are discussed. (C) 1997 Elsevier Science Ltd.