The Synthesis of Anthracene Crown Ethers Derived from Benzo-Crown Ethers. -A method to obtain anthracene crown ethers starting from benzo-15-crown-5-ether and benzo-18-crown-6-ether and various aldehydes is described. The yield strictly depends on the aldehyde. Cyclohexanone leads to a new class of
The synthesis of anthracene crown ethers derived from benzo-crown ethers
โ Scribed by Ryszard Ostaszewski
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 431 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
The sulfuric acid-promoted reaction of benzo-15-crown-5 O) and benzo-18-crown-6 (6) with aliphatic aldehydes, leading to the formation of anthracene crown et~rs, was studied. A substantial substiment effect on the reaction comse was found. For the isdmtyi group the highest yield was obtained, while for longer and shorter alkyl groups the yield dropped down. Reaction of aco.aldehyde and benzo-15crown-5 leads to formation of compound 4 in 35% yield. Application of cyclohexanone as a ca~nyl reagent caused formation of till now unknown 4,5-disubstituted crown ether 8.
๐ SIMILAR VOLUMES
A series of benzo-crown ethers containing the thiazole subcyclic moity have been synthesized. Reaction of 1,2-bis(thioamidomethyloxy)benzene 2 with ethyl bromopyruvate in ethanol provided 1,2-bis(thiazolyl)benzene \(4(80 \%)\) along with thiazole \(5(14 \%)\). Reduction of 4 with lithium aluminum hy
The synthesis of some novel benzo-crown ethers by =-amidomethylation is described. ~-Amidomethylation at carbon (the Chernyak-Einhorn reaction) has been the subject of numerous articles and reviews [2, 3], but there have been no reports of the use of benzocrown ethers in such reactions, and only a