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

来源：

CHEMICAL REVIEWS | 2003年 / 103卷 / 04期

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

[11] Bromine-magnesium exchange in gem-dibromocyclopropanes using Grignard reagents [J].

Baird, MS ;

Nizovtsev, AV ;

Bolesov, IG .

TETRAHEDRON, 2002, 58 (08) :1581-1593

[12] Intramolecular trapping of esters by 1-lithio-1-bromocyclopropanes [J].

Baird, MS ;

Huber, FAM ;

Tverezovsky, VV ;

Bolesov, IG .

TETRAHEDRON, 2000, 56 (27) :4799-4810

[13] (R)-1,3-DIMETHYLCYCLOPROPENE - ONE ISOMER OF THE SMALLEST CHIRAL HYDROCARBON [J].

BAIRD, MS ;

FITTON, HL ;

CLEGG, W ;

MCCAMLEY, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03) :321-326

[14] THE PREPARATION AND LITHIATION OF 1-HALOGENOCYCLOPROPENES [J].

BAIRD, MS ;

HUSSAIN, HH ;

NETHERCOTT, W .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (10) :1845-1853

[15] Construction of a tube-like molecule via sequential cyclopropylidene dimerisation and intramolecular [pi 2s+pi 2s] cycloaddition reactions [J].

Banwell, MG ;

Hockless, DCR ;

Walter, JM .

CHEMICAL COMMUNICATIONS, 1996, (12) :1469-1470

[16] Observations relating to the mode of formation of cyclopropylidene dimers in the reaction of gem-dibromocyclopropanes with methyllithium [J].

Banwell, MG ;

Hockless, DCR ;

Longmore, RW ;

Walter, JM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (05) :457-462

[17] KINETICS OF REACTIONS OF CYCLOPROPYLCARBINYL RADICALS AND ALKOXYCARBONYL RADICALS CONTAINING STABILIZING SUBSTITUENTS - IMPLICATIONS FOR THEIR USE AS RADICAL CLOCKS [J].

BECKWITH, ALJ ;

BOWRY, VW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2710-2716

[18] CYCLOADDITIONS AND ITERATIVE CYCLOADDITIONS WITH ACCEPTOR-SUBSTITUTED CYCLOPROPYLALKYNES [J].

BENGTSON, G ;

KEYANIYAN, S ;

DEMEIJERE, A .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (12) :3607-3630

[19] Ring opening of substituted cyclopropylidenes to cyclic allenes [J].

Bettinger, HF ;

Schleyer, PV ;

Schreiner, P ;

Schaefer, HF .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9267-9275

[20] Ring opening of cyclopropylidene and internal rotation of allene [J].

Bettinger, HF ;

Schreiner, PR ;

Schleyer, PV ;

Schaefer, HF .

JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (40) :16147-16154

← 1 2 3 4 5 6 7 8 9 10 →