Syntheses of gem-dihalocyclopropanes and their use in organic synthesis

被引:338
作者
Fedorynski, M [1 ]
机构
[1] Tech Univ Warsaw, Fac Chem, PL-00662 Warsaw, Poland
关键词
D O I
10.1021/cr0100087
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review demonstrates that the syntheses of gem-dihalocyclopropane derivatives can be accomplished by several highly efficient procedures, among which the phase-transfer catalytic method is the method of choice. The general concept of PTC and its basic mechanistic features are discussed, along with its major benefits and advantages in the chemistry of dihalocarbenes and gem-dihalocyclopropanes. The main types of gem-dihalocyclopropane transformations that have been described in recent years are discussed. Some transformations of 1,1-dihalo-2-phenylcyclopropanes are shown to illustrate the importance of this type of reaction.
引用
收藏
页码:1099 / 1132
页数:34
相关论文
共 50 条
[42]   Stereoselective Synthesis of endo-7-Halo-3-Oxo-2-Azabicyclo[4.1.0]Heptanes by Reductive Hydrodehalogenation of gem-Dihalocyclopropanes [J].
Joseph, Jomy K. ;
Singhal, Sweety ;
Jain, Suman L. ;
Sain, Bir .
CURRENT ORGANIC CHEMISTRY, 2011, 15 (08) :1230-1235
[43]   RING-OPENING OF GEM-DIHALOCYCLOPROPANES - NOVEL TYPES OF 1,4-ELIMINATION REACTIONS [J].
BESSARD, Y ;
KUHLMANN, L ;
SCHLOSSER, M .
TETRAHEDRON, 1990, 46 (15) :5230-5236
[44]   EFFICIENT METHOD FOR THE SYNTHESIS OF MONOHALOCYCLOPROPANES BY REDUCTION OF GEM-DIHALOCYCLOPROPANES WITH I-BU2ALH IN THE PRESENCE OF TI AND ZR COMPLEXES [J].
DZHEMILEV, UM ;
GAISIN, RL ;
TURCHIN, AA ;
KHALIKOVA, NR ;
BAIKOVA, IP ;
TOLSTIKOV, GA .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1990, 39 (05) :967-974
[45]   CHEMISTRY OF GEM-DIHALOCYCLOPROPANES .20. THE EFFECT OF METHYL AND PHENYL SUBSTITUENTS ON THE VINYLCYCLOPROPYLIDENE CYCLOPENTENYLIDENE REARRANGEMENT [J].
HOLM, KH ;
SKATTEBOL, L .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (09) :783-794
[46]   CHEMISTRY OF GEM-DIHALOCYCLOPROPANES .12. PREPARATION OF GEM-DIBROMOCYCLOPROPYL KETONES AND ALKYL GEM-DIBROMOCYCLO-PROPANECARBOXYLATES UNDER PHASE TRANSFER CONDITIONS [J].
SYDNES, LK .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1977, 31 (09) :823-825
[47]   CHEMISTRY OF GEM-DIHALOCYCLOPROPANES .22. INTRAMOLECULAR ADDITION OF CYCLOPROPYLIDENES TO ALIPHATIC AND AROMATIC DOUBLE-BONDS - A SYNTHESIS OF 2-ALKENYLTROPONES [J].
SKATTEBOL, L ;
NILSEN, NO ;
MYHREN, F .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (10) :782-790
[48]   REACTIONS OF GEM-DIHALOCYCLOPROPANES .3. SILVER-ASSISTED TRANSFORMATIONS OF 7,7-DIBROMOBICYCLO[4.1.0]HEPTANE [J].
ARCT, J ;
PRAWDA, A ;
KOZYRIEV, V .
BULLETIN DE L ACADEMIE POLONAISE DES SCIENCES-SERIE DES SCIENCES CHIMIQUES, 1978, 26 (07) :523-526
[49]   HALOMETHYL-METAL COMPOUNDS .2. PREPARATION OF GEM-DIHALOCYCLOPROPANES BY REACTION OF PHENYL(TRIHALOMETHYL)MERCURY COMPOUNDS WITH OLEFINS [J].
SEYFERTH, D ;
BURLITCH, JM ;
MINASZ, RJ ;
MUI, JYP ;
SIMMONS, HD ;
TREIBER, JH ;
DOWD, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (19) :4259-&
[50]   CHEMISTRY OF GEM-DIHALOCYCLOPROPANES .19. FORMATION OF 3-OXABICYCLO[3.1.0]HEXANE DERIVATIVES BY INTRAMOLECULAR INSERTION OF CYCLOPROPYLIDENES [J].
ARCT, J ;
SKATTEBOL, L ;
STENSTROM, Y .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (08) :681-686