From vinyl sulfides, sulfoxides and sulfones to vinyl zirconocene derivatives

被引：53
作者：
Farhat, S [1 ]
Zouev, I [1 ]
Marek, I [1 ]
机构：
[1] Technion Israel Inst Technol, Dept Chem, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel
来源：
TETRAHEDRON | 2004年 / 60卷 / 06期
基金：
以色列科学基金会;
关键词：
D O I：
10.1016/j.tet.2003.08.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An easy and straightforward new method for the preparation of Sp(2) zirconocene derivatives from a wide range of heterosubstituted alkenes such as vinyl sulfides, sulfoxides and sulfones is described. In all cases, a complete isomerization of the stereochemistry is observed and only the E-isomer is obtained. The reactivity of the resulting vinylic organometallic can be increased by a transmetalation reaction into organocopper, organozinc or organopalladium species and, therefore, several carbon-carbon formation were easily realized. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1329 / 1337
页数：9
相关论文
共 50 条
[41]   BONDING PARAMETERS AT S IN SULFIDES SULFOXIDES AND SULFONES [J].
HAUBACK, BC ;
MO, F .
ACTA CRYSTALLOGRAPHICA SECTION A, 1984, 40 :C266-C266
[42]   Green Organocatalytic Oxidation of Sulfides to Sulfoxides and Sulfones [J].
Voutyritsa, Errika ;
Triandafillidi, Ierasia ;
Kokotos, Christoforos G. .
SYNTHESIS-STUTTGART, 2017, 49 (04) :917-924
[43]   New procedures for the oxidation of sulfides to sulfoxides and sulfones [J].
Drabowicz, J ;
Lyzwa, P ;
Luczak, J ;
Mikolajczyk, M ;
Laur, P .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 120 :425-426
[44]   COMPARATIVE-STUDY OF SULFIDES, SULFOXIDES AND ORGANIC SULFONES USING VIBRATION SPECTROMETRY .1. SULFIDES, SULFOXIDES, AND DIMETHYL SULFONES [J].
CHASSAING, G ;
CORSET, J ;
LIMOUZI, J .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1981, 37 (09) :721-726
[45]   Conversion of cyclic vinyl sulfones to transposed vinyl phosphonates [J].
Noshi, Mohammad N. ;
El-Awa, Ahmad ;
Torres, Eduardo ;
Fuchs, Philip L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :11242-11247
[46]   Conversion of cyclic vinyl sulfones to transposed vinyl phosphonates [J].
Noshi, Mohammad N. ;
El-awa, Ahmad ;
Torres, Eduardo ;
Fuchs, Philip L. .
Journal of the American Chemical Society, 2007, 129 (36) :11242-11247
[47]   Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides [J].
Collins, Niall ;
Connon, Robert ;
Sanchez-Sanz, Goar ;
Evans, Paul .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (39) :6228-6235
[48]   ORGANIC SULFUR DERIVATIVES .2. SULFIDES, SULFOXIDES AND SULFONES FROM THIOLS AND 10-UNDECENOIC ACID [J].
KOENIG, NH ;
SWERN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (15) :4235-4237
[49]   Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones [J].
Roy, Tamal ;
Lee, Ji-Woong .
SYNLETT, 2020, 31 (05) :455-458
[50]   Stereoelectronic Effects in Vinyl Sulfoxides [J].
Ulshoefer, Roland ;
Podlech, Joachim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :16618-+
12345