High Quality 9-Anthracenemethanol 1468-95-7 Best Price CAS NO.1468-95-7

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High Quality 9-Anthracenemethanol 1468-95-7 Best Price

Properties

Description

9-Anthracenemethanol (Cas No.: 1468-95-7) participates in ring-opening polymerization of L-lactide catalyzed by alumoxane. It undergoes proton exchange reaction with potassium tert-butoxide to yield potassium 9-anthracenemethoxide.

9-Anthracenemethanol is the derivative of anthracene with a hydroxymethyl group (CH2OH) attached to the 9-position. It is a colorless solid that is soluble in ordinary organic solvents. The compound can be prepared by hydrogenation of 9-anthracenecarboxaldehyde. It is a versatile precursor to supramolecular assemblies.

Application

9-Anthracenemethanol can be used:

As a starting material to prepare 9-anthracenylmethyl-1-piperazinecarboxylate, which acts as a reagent in the determination of isocyanates using HPLC.

In the Diels-Alder reaction with dimethylacetylene-dicarboxylate to yield lactone derivatives.

As an initiator in the ring-opening polymerization of δ-valerolactone to yield poly(δ-valerolactone).

As a starting material in the synthesis of polymer-supported anthracene, which acts as a dienophile scavenger in cycloaddition reactions.

Preparation Products

9-(Pent-4-yn-1-yl)anthracene-type compounds can potentially undergo intramolecular Diels-Alder (IMDA) reaction to form 9,11-annulated dibenzobarrelenes. Herein we report the synthesis and IMDA reactions of several heteroatom incorporated 9-(pent-4-yn-1-yl)anthracene-type compounds.

Synthesis of bicyclo[2,2,2]octa-2,5,7-triene (barrelene) was first reported by Zimmerman1 et al in 1960. Its

barrel-shaped array of molecular orbitals and three ethylene units that are like staves attached to the two

methine units attracted the attention of chemists. Synthesis of several barrelene derivatives, especially

dibenzobarrelenes, exploited Diels-Alder reaction.2-7 Intramolecular Diels-Alder (IMDA) reaction of suitably

substituted anthracenes to give tricyclic systems that may be regarded as annulated barrelenes was first

reported by Meek and Dann.8,9 In 1980, Ciganek5 reported a systematic investigation on the synthesis of 9,11-

bridged dibenzobarrelene via IMDA reaction (Scheme 1). Entropically favoured IMDA reaction generally

proceeded with increased reaction rates under mild reaction conditions and the products were obtained in

good yield.

Scheme 1

Barrelene undergoes singlet mediated rearrangement to give cyclooctatetraene and triplet mediated di-π

methane rearrangement10-12 to afford semibullvalene. Initially, diverse photochemistry of dibenzobarrelenes

occupied center stage and most attempts on dibenzobarrelene synthesis were directed towards deciphering

the effect of substituents on controlling the photochemistry of barrelenes.13 However chemistry of barrelenes

has now transcended to encompass several fields including recently found applications in OLEDs14 and

photoluminescent materials.15,16Dibenzobarrelene based azaacenes found enhanced device performance than

corresponding appended iptycene motifs.14 Dibenzobarrelenes have been exploited in the biological field also;

dibenzobarrelene fused with thiazole and thiophene entities showbiological activities17 and are employed in

drug discovery. In this context, we explored the possibility of synthesizing different types of 9,11-annulated

barrelenes with ester, ether, sulfide and sulfone tethers constructed between 9- and 11-positions in the newly

synthesized barrelenes.

 

Result and Discussion

We employed IMDA strategy to generate several 9,11-bridged dibenzobarrelenes where ester, sulfide, sulfone

and ether linkages constituted the putative 9,11-bridges. As expected, IMDA reactions proceeded under mild

conditions with high reaction rates. Structure of IMDA adducts were arrived at on the basis of spectral and

analytical data and single crystal X-ray diffraction studies on a few representative examples. Structure of 9-

(pent-4-yn-1-yl)anthracene-type compounds (3,4) and their IMDA products (5,6,7,8) are listed in Figure 1.

Steps involved in the synthesis of 9-(pent-4-yn-1-yl)anthracene-type compounds and their respective IMDA

products are depicted in Scheme 2.

 

Company Information

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