Allenes from cyclopropanes and their use in organic synthesis - Recent developments

被引:356
作者
Sydnes, LK [1 ]
机构
[1] Univ Bergen, Dept Chem, NO-5007 Bergen, Norway
关键词
CIS-TRANS PHOTOISOMERIZATION; DIELS-ALDER REACTION; GEM-DIHALOCYCLOPROPANES; CARBENE-DIMERIZATION; INTRAMOLECULAR ADDITION; GRIGNARD-REAGENTS; SUBSTITUTED CYCLOPROPYLIDENES; BIRADICAL CYCLIZATION; THERMAL GENERATION; CARBOXYLIC-ACIDS;
D O I
10.1021/cr010025w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The discovery of the alkylithium-induced conversion of gem-dihalocyclopropanes to allenes generated a lot of activity among experimental and theoretical chemists alike, and a large number of studies were initiated to uncover the chemical properties of halogenated and nonhalogenated cyclopropanes. However, many of the transformations that were discovered were either impractical or so limited in scope that they were barely used and made little impact before they drifted out of focus. Therefore cyclopropane chemistry has become less important for the development and use of allene chemistry. However, recent developments reversed this scenario.
引用
收藏
页码:1133 / 1150
页数:18
相关论文
共 172 条
[1]   PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES [J].
AHMAR, M ;
ANTRAS, F ;
CAZES, B .
TETRAHEDRON LETTERS, 1995, 36 (25) :4417-4420
[2]   Hydrodehalogenation of 1,1-dibromocyclopropanes by Grignard reagents promoted by titanium compounds [J].
Al Dulayymi, JR ;
Baird, MS ;
Bolesov, IG ;
Nizovtsev, AV ;
Tverezovsky, VV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, Royal Society of Chemistry (07) :1603-1617
[3]   1,2-DIBROMOALK-2-ENYLIDENES BY RING-OPENING OF 1,2-DIBROMO-3-ALKYLCYCLOPROPENES AT AMBIENT-TEMPERATURE [J].
ALDULAYYMI, JR ;
BAIRD, MS ;
FITTON, HL ;
RAJARAM, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (12) :1633-1641
[4]   A DIRECT AND A FORMAL TRAPPING OF PROPA-1,2-DIENYLIDENE [J].
ALDULAYYMI, JR ;
BAIRD, MS .
TETRAHEDRON LETTERS, 1995, 36 (19) :3393-3396
[5]   THE STEREOCHEMISTRY OF RING-OPENING OF 3-ALKYL-1,1-DIHALOCYCLOPROPENES TO VINYLCARBENES AT AMBIENT-TEMPERATURE [J].
ALDULAYYMI, JR ;
BAIRD, MS ;
FITTON, HL .
TETRAHEDRON LETTERS, 1992, 33 (33) :4803-4806
[6]   The first generation and trapping of a five-membered ring allene:: 2-dehydro-3a,4,5,6,6a-pentahydropentalene [J].
Algi, F ;
Özen, R ;
Balci, M .
TETRAHEDRON LETTERS, 2002, 43 (17) :3129-3131
[7]  
BACKES J, 1989, HOUBEN WEYL ME E B 1, V19, P430
[8]   1-HALOCYCLOPROPENES AND PROPARGYLIC HALIDES FROM THE REACTION OF TRIHALOCYCLOPROPANES WITH METHYL LITHIUM [J].
BAIRD, MS ;
NETHERCOTT, W .
TETRAHEDRON LETTERS, 1983, 24 (06) :605-608
[9]   LABELING STUDIES OF THE RING-OPENING OF 1-BROMO-2-CHLORO-3,3-DIMETHYLCYCLOPROPENE [J].
BAIRD, MS .
TETRAHEDRON LETTERS, 1984, 25 (42) :4829-4832