Synthesis of perfluorinated allylic compounds by radical allylation and their purification over fluorous reverse-phase silica

被引：35

作者：

Ryu, IY ^{[1
]}

Kreimerman, S

Niguma, T

Minakata, S

Komatsu, M

Luo, ZY

Curran, DP

机构：

[1] Osaka Prefecture Univ, Fac Arts & Sci, Dept Chem, Sakai, Osaka 5998531, Japan

[2] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[3] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[4] Univ Pittsburgh, Ctr Combinatorial Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 05期

基金：

美国国家科学基金会; 日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(00)02153-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple free-radical method for the preparation of a variety of perfluorinated allylic compounds has been developed starting from perfluoroalkyl iodides and allyltins. Allyltributyltin, methallyltributyltin and crotyltributyltin all proved to be useful For the transformation. The desired perfluorinated allylic compound was conveniently isolated from the crude mixture by solid-phase extraction with fluorous reverse-phase silica (FRPS). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：947 / 950

页数：4

共 34 条

[1] Additions of PH3 to monosubstituted alkenes of the formula H2C=CH(CH2)x(CF2)yCF3:: Convenient, multigram syntheses of a family of partially fluorinated trialkylphosphines with modulated electronic properties and fluorous phase affinities
Alvey, LJ
Rutherford, D
Juliette, JJJ
Gladysz, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) : 6302 - 6308
[2] Synthesis of hybrid fluorinated silicones .1. Influence of the spacer between the silicon atom and the fluorinated chain in the preparation and the thermal properties of hybrid homopolymers
Ameduri, B
Boutevin, B
GuidaPietrasanta, F
Manseri, A
Ratsimihety, A
Caporiccio, G
[J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1996, 34 (15) : 3077 - 3090
[3] CHAMBERS ED, 1997, TOPICS CURRENT CHEM, V192
[4] CHAMBERS ED, 1997, TOPICS CURRENT CHEM, V193
[5] Chemistry of acyl radicals
Chatgilialoglu, C
Crich, D
Komatsu, M
Ryu, I
[J]. CHEMICAL REVIEWS, 1999, 99 (08) : 1991 - 2069
[6] STEREOSELECTIVE SYNTHESIS OF (E)-VINYLSTANNANES FROM ALDEHYDES
CHONG, JM
PARK, SB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 523 - 527
[7] Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel
Curran, DP
Luo, ZY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) : 9069 - 9072
[8] Thermal allylations of aldehydes with a fluorous allylstannane. Separation of organic and fluorous products by solid phase extraction with fluorous reverse phase silica gel
Curran, DP
Hadida, S
He, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 6714 - 6715
[9] Curran DP, 1998, MED CHEM RES, V8, P261
[10] Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions
Curran, DP
Hadida, S
Kim, SY
Luo, ZY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) : 6607 - 6615

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