Controlled monohalogenation of phosphonates:: A new route to pure α-monohalogenated diethyl benzylphosphonates

被引：55

作者：

Iorga, B ^{[1
]}

Eymery, F ^{[1
]}

Savignac, P ^{[1
]}

机构：

[1] Ecole Polytech, UMR CNRS 7653, Lab Heteroatomes & Coordinat, DCPH, F-91128 Palaiseau, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(99)00037-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from diethyl benzylphosphonates, a wide variety of diethyl alpha-monofluoro, chloro, bromo and iodobenzylphosphonates have been obtained in pure form by a one-pot procedure. This high yielding method implies the intermediate protection of the benzyl anion with TMSCI followed by halogenation with an electrophilic halogenating reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2671 / 2686

页数：16

共 36 条

[1] Arbuzov A.E., 1906, J RUSS PHYS CHEM SOC, V38, P687
[2] BERGMANN ED, 1968, ISRAEL J CHEM, V6, P73
[3] A NOVEL SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (11) : 511 - 513
[4] SYNTHESIS OF ALPHA-FLUOROALKYLPHOSPHONATES AND GAMMA-FLUOROALKYLPHOSPHONATES
BLACKBURN, GM
KENT, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 913 - 917
[5] CABARES J, 1986, B SOC CHIM FR, P401
[6] 2-DIETHOXYPHOSPHORYL ALCANOIC ACID DIANIONS (LITHIUM ALPHA-LITHIOCARBOXYLATES) .4. A DIRECT ROUTE TO 2-FLUORO-2-ALKENOIC ACIDS BY THE HORNER SYNTHESIS - APPLICATION IN THE FIELD OF PYRETHROIDS
COUTROT, P
GRISON, C
SAUVETRE, R
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 332 (1-2) : 1 - 8
[7] AROMATIC RETINOIC ACID ANALOGS .2. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY
DAWSON, MI
CHAN, R
HOBBS, PD
CHAO, WR
SCHIFF, LJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (09) : 1282 - 1293
[8] ELKIK E, 1986, B SOC CHIM FR, P423
[9] ETEMADMOGHADAM G, 1985, B SOC CHIM FR, P448
[10] FRANKE A, 1979, SYNTHESIS-STUTTGART, P712

← 1 2 3 4 →