Helical chirality of new pyrrolo[1,2-a][1,10]phenanthrolines

被引：0

作者：

Dumitrascu, F ^{[1
]}

Mitan, CI ^{[1
]}

Draghici, C ^{[1
]}

Caproiu, MT ^{[1
]}

Raileanu, D ^{[1
]}

机构：

[1] Romanian Acad, Inst Organ Chem CD Nenitzescu, R-71141 Bucharest 15, Romania

来源：

REVISTA DE CHIMIE | 2002年 / 53卷 / 12期

关键词：

1,10-phenanthrolinium N-ylides; 1,3-dipolar cycladditions; pyrrolo[1,2-a][1,10]phenantrolines; helical chirality;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,3-dipolar cycloadditions between 1-(4-methylphenacyl)-1,10-phenantrolinium ylide 4 and dimethyl, diethyl or diisopropyl esters of acetylenedicarboxylic acid gave pyrrolo[1,2-a][1,10]phenantrolines 7a-c. The helical chirality of ethyl (7b) and isopropyl esters (7c) was put in evidence by H-1-NMR spectroscopy and the activation free energy was estimated from the coalescence. Treatment of ylide 4 with acetylenic esters at room temperature gave regio- and stereospecifically a mixture of cis-3,3a-dihydro-pyrrolophenantrolines 6 along with variable amounts of 7.

引用

页码：787 / 790

页数：4

共 7 条

[1] SOME 1,3-DIPOLAR ADDITION REACTIONS OF ISOQUINOLINIUM YLIDES - FORMATION OF 2,3-DIHYDROBENZO[G]INDOLIZINES AND BENZOINDOLIZINES
BASKETTE.N
PLUNKETT, AO
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (23): : 1578 - &
[2] CALDER IC, 1968, J AUST CHEM, V21, P1023
[3] Primary cycloadducts of 1,10-phenanthrolinium and phthalazinium phenacylides with DMAD
Dumitrascu, F
Mitan, CI
Draghici, C
Caproiu, MT
Raileanu, D
[J]. TETRAHEDRON LETTERS, 2001, 42 (47) : 8379 - 8382
[4] Eliel E. L., 1994, STEREOCHEMISTRY ORGA, P1163
[5] KUTSUMA T, 1972, CHEM PHARM BULL, V20, P2701
[6] SANDSTROM L, 1982, DYNAMIC NMR SPECTROS
[7] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF GEOMETRICAL ISOMERS OF SOME METHYL 1-ALKYL-2-(P-BIPHENYL)-3-AZIRIDINECARBOXYLATES
WOLLER, PB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) : 888 - &

← 1 →