A high yielding preparation of α-trimethylsilyloxyphosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine

被引：79

作者：

Firouzabadi, H ^{[1
]}

Iranpoor, N ^{[1
]}

Sobhani, S ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Shiraz 71454, Iran

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(02)00631-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, versatile, high yielding and convenient procedure for the immediate conversion of various alpha-hydroxyphosphonates to alpha-trimethylsilyloxyphosphonates under neutral conditions using HMDS in the presence of a catalytic amount of iodine is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：3653 / 3655

页数：3

相关论文

共 18 条

[1]

BARALDI PG, 1982, SYNTHESIS-STUTTGART, P653

[2]

BIRUM GH, 1963, Patent No. 3113139

[3]

ERNST A, 1990, SYNTHESIS-STUTTGART, P323

[4]

EVANS DA, 1977, TETRAHEDRON LETT, V29, P2495

[5] Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions and potassium permanganate in dry benzene [J].

Firouzabadi, H ;

Iranpoor, N ;

Sobhani, S .

TETRAHEDRON LETTERS, 2002, 43 (03) :477-480

[6] High yield preparation of a-ketophosphonates by oxidation of α-hydroxyphosphonates with zinc dichromate trihydrate (ZnCr2O7•3H2O) under solvent-free conditions [J].

Firouzabadi, H ;

Iranpoor, N ;

Sobhani, S ;

Sardarian, AR .

TETRAHEDRON LETTERS, 2001, 42 (26) :4369-4371

[7]

HATA T, 1978, TETRAHEDRON LETT, V4, P363

[8]

KABACHNIK MM, 1990, VESTN MOSK U KHIM+, V31, P384

[9] Mild and highly efficient method for the silylation of alcohols using hexamethyldisilazane catalyzed by iodine under nearly neutral reaction conditions [J].

Karimi, B ;

Golshani, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7228-7230

[10] ALPHA-HETEROSUBSTITUTED PHOSPHONATE CARBANIONS .9. DIETHYL 1-PHENYL -1-TRIMETHYLSILOXYMETHANE PHOSPHONATE AS AN ACYL ANION EQUIVALENT - NOVEL METHOD FOR THE PREPARATION OF ALPHA-HYDROXYKETONES [J].

KOENIGKRAMER, RE ;

ZIMMER, H .

TETRAHEDRON LETTERS, 1980, 21 (11) :1017-1020