Unknown

Dataset Information

0

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives.


ABSTRACT: When 9,10-dibromoanthracene was treated with bromine in CCl(4) without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene (3) was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide 3 under various conditions. Pyridine-induced elimination of hexabromide 3 afforded 2,9,10-tribromoanthracene (12) in 75% yield, and tribromide 12 was transformed to trimethoxy compound 13 and trinitrile 14 by copper-assisted nucleophilic substitution reactions.

SUBMITTER: Cakmak O 

PROVIDER: S-EPMC2633663 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature

altmetric image

Publications

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives.

Cakmak Osman O   Aydogan Leyla L   Berkil Kiymet K   Gulcin Ilhami I   Buyukgungor Orhan O  

Beilstein journal of organic chemistry 20081210


When 9,10-dibromoanthracene was treated with bromine in CCl(4) without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene (3) was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide 3 under various conditions. Pyridine-induced elimination of hexabromide 3 afforded 2,9,10-tribromoanthracene (12) in 75% yield, and tribromide 12 was transformed to trimethoxy compound 13 and trinitr  ...[more]

Similar Datasets

| S-EPMC3484212 | biostudies-literature
| S-EPMC6136266 | biostudies-literature
| S-EPMC6273136 | biostudies-literature
| S-EPMC8470325 | biostudies-literature
| S-EPMC4015188 | biostudies-literature
| S-EPMC3167179 | biostudies-literature
| S-EPMC8152782 | biostudies-literature
| S-EPMC5903033 | biostudies-literature
| S-EPMC6271259 | biostudies-literature
| S-EPMC6707873 | biostudies-literature