Prepackaged Ramberg-Backlund reagents: useful tools for organic synthesis

被引:11
作者
Block, E [1 ]
Jeon, HR [1 ]
Putman, D [1 ]
Zhang, SZ [1 ]
机构
[1] SUNY Albany, Dept Chem, Albany, NY 12222 USA
基金
美国国家科学基金会;
关键词
Ramberg-Backlund reaction; alpha-halosulfones;
D O I
10.1016/j.tet.2004.06.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and reactions of several mu,beta-unsaturated chloromethyl sulfones is presented, for example [(chloromethyl)-sulfonyl]-1,3-propadiene (4), [(chloromethyl)sulfonyl]ethene (5), [(dichloromethyl)sulfonyl]ethene (6) and (E,Z)-1,2-bis[(chloromethyl)-sulfonyl]ethene (7). These compounds serve as 'prepackaged' Ramberg-Backlund reagents, which following an appropriate first step, such as Diels-Alder addition, react with base giving Ramberg-Backlund products. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7525 / 7541
页数:17
相关论文
共 41 条
[1]   ALPHA-METHYLENE-BETA-LACTONES AS NOVEL ALLENE EQUIVALENTS - REGIOSELECTIVE [4+2]-CYCLOADDITION AND STEREOSELECTIVE DECARBOXYLATION FOR THE INTRODUCTION OF EXO-ALKYLIDENE FUNCTIONALITIES [J].
ADAM, W ;
HASEMANN, L .
TETRAHEDRON LETTERS, 1991, 32 (48) :7033-7036
[2]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[3]   UBER EINIGE BICYCLISCHE TRIENE MIT ORTHO-DIMETHYLEN-STRUKTUR [J].
ALDER, K ;
HARTUNG, S ;
NETZ, O .
CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (01) :1-7
[4]   Aromatic heterocycles containing arsenic and sulfur: The synthesis of 1,2- and 1,3-thiaarsole and the gas-phase molecular structure of 1,2-thiaarsole [J].
Ashe, AJ ;
Fang, XG ;
Schiesher, M ;
Richardson, AD ;
Hedberg, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :7012-7016
[5]   CYCLIC DIENES .22. SUBSTITUTED 1,2-DIMETHYLENE-4-CYCLOHEXENES [J].
BAILEY, WJ ;
HUDSON, RL ;
LIAO, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (16) :4358-4360
[6]   CYCLIC DIENES .11. NEW SYNTHESES OF HEXACENE AND HEPTACENE [J].
BAILEY, WJ ;
LIAO, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :992-993
[7]   ALPHA-HALOALKANESULFONYL BROMIDES IN ORGANIC-SYNTHESIS .5. VERSATILE REAGENTS FOR THE SYNTHESIS OF CONJUGATED POLYENES, ENONES, AND 1,3-OXATHIOLE 1,1-DIOXIDES [J].
BLOCK, E ;
ASLAM, M ;
ESWARAKRISHNAN, V ;
GEBREYES, K ;
HUTCHINSON, J ;
IYER, R ;
LAFFITTE, JA ;
WALL, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4568-4580
[8]   Chloromethanesulfonylethene and dichloromethanesulfonylethene: New reagents for tandem Diels-Alder/Ramberg-Backlund reactions [J].
Block, E ;
Jeon, HR ;
Zhang, SZ ;
Dikarev, EV .
ORGANIC LETTERS, 2004, 6 (03) :437-440
[9]   ALPHA-HALOALKANESULFONYL BROMIDES IN ORGANIC-SYNTHESIS .1. FORMATION AND BASE-INDUCED REACTIONS OF ALPHA,BETA-UNSATURATED HALOMETHYL SULFONES [J].
BLOCK, E ;
ASLAM, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6164-6165
[10]   ALPHA-HALOALKANESULFONYL BROMIDES IN ORGANIC-SYNTHESIS .4. REGIOSELECTIVE GAMMA-DEPROTONATION OF ALPHA,BETA-UNSATURATED SULFONES - A SIMPLE SYNTHESIS OF 2-ALKYL-1,3-BUTADIENES [J].
BLOCK, E ;
ESWARAKRISHNAN, V ;
GEBREYES, K .
TETRAHEDRON LETTERS, 1984, 25 (48) :5469-5472