Selenylated dienes:: synthesis, stereochemical studies by 77Se NMR, and transformation into functionalized allenes

被引：12
作者：
Redon, Sebastien [1 ]
Berkaoui, Anne-Lise Berthe [1 ]
Pannecoucke, Xavier [1 ]
Outurquin, Francis [1 ]
机构：
[1] Univ Rouen, LHO, IRCOF, CNRS,UMR 6014, F-76821 Mont St Aignan, France
来源：
TETRAHEDRON | 2007年 / 63卷 / 18期
关键词：
selenium; allenes; oxidation; conjugated dienes;
D O I：
10.1016/j.tet.2007.02.082
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Phenylselanyl-1,3-dienes 3-8 were prepared by a Wittig or Wittig-Horner-Emmons procedure starting from alpha-phenylselanyl alpha,beta-unsaturated aldehydes. Ratio and configuration of each diene isomers were determined by Se-77 and H-1 NMR. These dienes were then oxidized into selenoxides, which could be isolated in some cases. In THF, [2,3]-sigmatropic rearrangement of allylic selenoxides, selenimides, and dihalo-selenuranes occurred, yielding allenyl alcohols 12-15, allenyl carbamates 16c-19c, and 1-haloalkyl allenes 20c-22c, respectively. (C) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：3707 / 3717
页数：11
相关论文
共 74 条
[1]   DIASTEREOSELECTIVE SYN OR ANTI OPENING OF PROPARGYLIC EPOXIDES - SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS [J].
ALEXAKIS, A ;
MAREK, I ;
MANGENEY, P ;
NORMANT, JF .
TETRAHEDRON, 1991, 47 (09) :1677-1696
[2]  
[Anonymous], 1987, Organoselenium Chemistry
[3]  
Back T. G., 1999, ORGANOSELENIUM CHEM
[4]   CONVENIENT SYNTHESIS AND CYCLOADDITION REACTIONS OF 2-PHENYLSELENO-1,3-BUTADIENE AND 2-TRIALKYLSTANNYL-1,3-BUTADIENES [J].
BATES, GS ;
FRYZUK, MD ;
STONE, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (11) :2612-2617
[5]   PHENYLTHIO MIGRATIONS IN REARRANGEMENTS OF 2,2-BISPHENYLTHIOETHANOLS [J].
BLATCHER, P ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05) :1055-1066
[6]   Synthesis of heterocycles by radical cyclisation [J].
Bowman, WR ;
Bridge, CF ;
Brookes, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01) :1-14
[7]  
Brandsma L., 1981, Synthesis of Acetylenes, Allenes, Cumulenes: A Laboratory Manual
[8]   THE DIELS-ALDER REACTIVITY OF SOME NEW SULFUR (SELENIUM) SUBSTITUTED HALOBUTADIENES [J].
BRIDGES, AJ ;
FISCHER, JW .
TETRAHEDRON LETTERS, 1983, 24 (05) :447-450
[9]   New developments with chiral electrophilic selenium reagents [J].
Browne, Danielle M. ;
Wirth, Thomas .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (15) :1893-1903
[10]  
Byers JH, 1998, HETEROCYCLES, V48, P2071
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