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

被引：22

作者：

Laws, MJ ^{[1
]}

Schiesser, CH ^{[1
]}

机构：

[1] UNIV MELBOURNE,SCH CHEM,PARKVILLE,VIC 3052,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 48期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)10239-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 57% yield, together with 1-(butyltelluro)-2-phenyl-2-propanol (7, 7%). This transformation presumably 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 butyltelluroate under similar conditions. Mechanistic and kinetic implications are discussed. (C) 1997 Elsevier Science Ltd.

引用

页码：8429 / 8432

页数：4

共 16 条

[11] Electrochemically induced S(RN)1 substitution of fluorinated aryl halides. Application to the synthesis of fluorinated-aryl heterocycles
Medebielle, M
Pinson, J
Saveant, JM
[J]. ELECTROCHIMICA ACTA, 1997, 42 (13-14) : 2049 - 2055
[12] S(RN)1 reactions of 7-iodobicyclo[4.1.0]heptane, 1-iodoadamantane, and neopentyl iodide with carbanions induced by FeBr2 in DMSO
Nazareno, MA
Rossi, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) : 1645 - 1649
[13] Petragnani N., 1994, TELLURIUM ORGANIC SY
[14] Free-radical homolytic substitution: New methods for formation of bonds to heteroatoms
Schiesser, CH
Wild, LM
[J]. TETRAHEDRON, 1996, 52 (42) : 13265 - 13314
[15] SCHIESSER CH, UNPUB
[16] SCHIESSER CH, 1997, IN PRESS J CHEM SOC

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