SELECTIVE SIDE-CHAIN OXIDATION OF PERALKYLATED PYRROMETHENE-BF2 COMPLEXES

被引：54

作者：

SATHYAMOORTHI, G ^{[1
]}

WOLFORD, LT ^{[1
]}

HAAG, AM ^{[1
]}

BOYER, JH ^{[1
]}

机构：

[1] UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148

来源：

HETEROATOM CHEMISTRY | 1994年 / 5卷 / 03期

关键词：

D O I：

10.1002/hc.520050309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidized 2,6-diethyl-1,3,5,7,8-pen-tamethylpyrromethene-BF2 complex 1, 13,14-tri-methyl-2, 3, 4, 5,9,10,11,12-octahydroindomethene-BF2 complex 5, and 1,3,5,7,8-pentamethyl-1,2,3, 5,6,7-hexahydropyrromethene-BF2 complex 8 to the weakly fluorescent 3-formyl, 5-oxo, and 8-formyl derivatives 4, 6, and 9, respectively. The dye 1 was oxidized by lead tetraacetate to 1,7,8-trimethyl-2,6-di-ethyl-3,5-diacetoxymethylpyrromethene-BF2 complex 12 [lambda(f) (ethanol) 538 nm, PHI 0.62, lambda(las) (ethanol) 555-570 nm]. Catalytic reduction (Pd/C) converted the aldehyde 4 to 2,6-diethyl-3-hydroxymethyl-1,5,7,8-te-tramethylpyrromethene-BF2 COMPlex 10 [lambda(f) (ethanol) 537 nm, PHI 0.70, lambda(las) (ethanol) 547-575 nm].

引用

页码：245 / 249

页数：5

共 17 条

[1] PYRROMETHENE-BF2 COMPLEXES AS LASER-DYES .2.
BOYER, JH
HAAG, AM
SATHYAMOORTHI, G
SOONG, ML
THANGARAJ, K
PAVLOPOULOS, TG
[J]. HETEROATOM CHEMISTRY, 1993, 4 (01) : 39 - 49
[2] DICHLORODICYANOQUINONE OXIDATIONS IN THE INDOLE AREA - SYNTHESIS OF CREATINE
CAIN, M
MANTEI, R
COOK, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) : 4933 - 4936
[3] Clezy P.S., 1970, AUST J CHEM, V23, P589, DOI 10.1071/ CH9700589
[4] deWael E. V., 1977, RECL TRAV CHIM PAY B, V96, P306, DOI 10.1002/recl.19770961205
[5] DEWAR MJS, 1969, MOL ORBITAL THEORY O, P304
[6] Lead tetracetat as oxidation agent.
Dimroth, O
Schweizer, R
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1923, 56 : 1375 - 1385
[7] SYNTHESIS OF (+/-)-CAMPHOR
FAIRLIE, JC
HODGSON, GL
MONEY, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (19): : 2109 - 2112
[8] EFFICIENT LASER ACTION FROM 2 CW LASER-PUMPED PYRROMETHENE-BF(2) COMPLEXES
GUGGENHEIMER, SC
BOYER, JH
THANGARAJ, K
SHAH, M
SOONG, ML
PAVLOPOULOS, TG
[J]. APPLIED OPTICS, 1993, 32 (21): : 3942 - 3943
[9] CLEAVAGE OF CARBON-OXYGEN BONDS - DIMETHYLBORON BROMIDE - A NEW REAGENT FOR ETHER CLEAVAGE
GUINDON, Y
YOAKIM, C
MORTON, HE
[J]. TETRAHEDRON LETTERS, 1983, 24 (29) : 2969 - 2972
[10] BENZYLIC OXIDATION WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN AQUEOUS-MEDIA - A CONVENIENT SYNTHESIS OF ARYL KETONES AND ALDEHYDES
LEE, H
HARVEY, RG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (05) : 749 - 751

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