Soluble and insoluble polymeric 1,3-dithiane reagents for the synthesis of aldehydes from alkyl halides

被引：7
作者：
Bertini, V [1 ]
Lucchesini, F [1 ]
Pocci, M [1 ]
Alfei, S [1 ]
机构：
[1] Univ Genoa, Dipartimento Chim & Tecnol Farmaceut & Alimentari, I-16147 Genoa, Italy
来源：
TETRAHEDRON | 2005年 / 61卷 / 40期
关键词：
supported reagents; umpolung reactions; 1,3-dithianes aldehydes; alkyl halides;
D O I：
10.1016/j.tet.2005.07.091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Through the synthesis and study of model systems as proper dithiane derivatives, vinyl monomers and soluble copolymeric reagents containing 2-unsubstituted 1,3-dithiane rings, we attained the key synthon 1,3-dithiane-5-methanol. Through its reaction with commercial resins, new polymeric reagents useful for supported organic synthesis and combinatorial chemistry were developed. Exploiting the reactivity of position 2 in 1,3-dithiane rings, such polymeric reagents were employed in the production of aldehydes from alkyl halides through a process entirely free from unpleasant odors. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9519 / 9526
页数：8
相关论文
共 21 条
[1]  
BARLUENGA J, 1986, SYNTHESIS-STUTTGART, P678
[2]   1,3-dithiane polymers for the supported synthesis of ketones [J].
Bertini, V ;
Lucchesini, F ;
Pocci, M ;
De Munno, A .
TETRAHEDRON LETTERS, 1998, 39 (50) :9263-9266
[3]   Polymeric reagents with propane-1,3-dithiol functions and their precursors for supported organic syntheses [J].
Bertini, V ;
Lucchesini, F ;
Pocci, M ;
De Munno, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4839-4842
[4]   Monomers containing substrate or inhibitor residues for copper amine oxidase and their hydrophilic beaded resins designed for enzyme interaction studies [J].
Bertini, V ;
Alfei, S ;
Pocci, M ;
Lucchesini, F ;
Picci, N ;
Iemma, F .
TETRAHEDRON, 2004, 60 (50) :11407-11414
[5]   Polystyrene resins containing 1,3-propanedithiol functions for solid-phase organic syntheses [J].
Bertini, V ;
Pocci, M ;
Lucchesini, F ;
Alfei, S ;
De Munno, A .
SYNLETT, 2003, (06) :864-866
[6]   Reductive cleavage of 1,3-dithiane systems anchored on polymers useful for supported organic syntheses [J].
Bertini, V ;
Lucchesini, F ;
Pocci, M ;
Alfei, S ;
De Munno, A .
SYNLETT, 2003, (08) :1201-1203
[7]   TRIMETHYLSILYL CYANIDE - REAGENT FOR UMPOLUNG .1. NUCLEOPHILIC ACYLATION OF ALKYLATING REAGENTS WITH AROMATIC AND HETEROAROMATIC ALDEHYDES [J].
DEUCHERT, K ;
HERTENSTEIN, U ;
HUNIG, S ;
WEHNER, G .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (06) :2045-2061
[8]   ORGANOSULFUR CHEMISTRY .2. HIGHLY STEREOSELECTIVE REACTIONS OF 1,3-DITHIANES - CONTRATHERMODYNAMIC FORMATION OF UNSTABLE DIASTEREOISOMERS [J].
ELIEL, EL ;
HARTMANN, AA ;
ABATJOGL.AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (06) :1807-1816
[9]   SYNTHESIS AND EVALUATION OF NOVEL ALKYLPIPERAZINES AS POTENTIAL DOPAMINE ANTAGONISTS [J].
GLENNON, RA ;
SALLEY, JJ ;
STEINSLAND, OS ;
NELSON, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (06) :678-683
[10]   THE CHEMISTRY OF SOME 5-M-DITHIANONES AND DITHIACYCLOALKANONES [J].
HOWARD, EG ;
LINDSEY, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (01) :158-164
123