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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.

Experimental Section

General. Melting points are uncorrected and recorded on a Neolab melting point apparatus. Infrared spectra

were recorded on Jasco 4100 and ABB Bomem (MB Series) FT-IR spectrometers. 1H and 13C NMR spectra were

recorded on 400 MHz Bruker Avance III FT-NMR spectrometer with tetramethylsilane (TMS) as internal

standard. Chemical shifts (δ) are reported in parts per million (ppm) downfield of TMS. Elemental analysis was

performed using Elementar Systeme (Vario EL III). Molecular mass was determined by electron impact (EI)

method using GC-MS (Agilent GC-7890A, Mass-5975C).

General procedure for the synthesis of bridged esters 5. Aldehydes 9 were synthesized via formylation18,19 of

anthracene by a known procedure. Aldehydes 9 (16 mmol) were oxidized with t-butyl hydroperoxide (1.92 mL,

20 mmol) and Se(IV) oxide (0.14 g, 1.25 mmol) (48-70h) in t-butanol at 75 o C. Undissolved materials were

filtered off and filtrate was evaporated. The residue thus obtained was dissolved in dichloromethane (120 mL)

and stirred with 5N HCl (200 mL) at room temperature for 4h. The aqueous and organic layers were separated

and from the aqueous layer, the acids were extracted with dichloromethane. The organic solutions were

collected and dried over anhydrous sodium sulfate and solvents were evaporated to obtain corresponding

acids 10 (76-80 % yield, Table 1). Triethylamine (1.40 mL, 10 mmol) was added to a solution of 10 (10 mmol)

and cyanuric chloride (1.84 g, 10 mmol) in acetone and stirred at room temperature for 1h to get the

corresponding acid chloride 12. Propargyl alcohol (0.60 mL, 10 mmol) was added into it (one pot reaction) and

the mixture was stirred for 4h. The products obtained were washed with sodium bicarbonate and extracted

with dichloromethane. Esters 13 were purified by silica gel column chromatography using a mixture of hexane

and dichloromethane as eluents. Pure products were obtained in 82-90 % yield. Anthracene derivatives

appended with acetylinic substituents 13 (5 mmol) were refluxed in p-xylene (10 mL) (48-64h) to generate

corresponding barrelenes 5 that were purified by silica gel column chromatography using a mixture of hexane

and dichloromethane as eluents (80-90% yield).

Table 1. Amount of reactants taken in each step of the reactions and yields of intermediates 10 and 13

General procedure for the synthesis of bridged sulfides 6. Aldehydes 9 (16 mmol) dissolved in methanol,

were reduced to corresponding alcohols 14 using sodium borohydride (1.1 g, 30 mmol) in methanol. Alcohols

14 (10 mmol) and two equivalents of thiourea (1.5 g, 20 mmol) were dissolved in acetone (25 mL) and 5N HCl

(5 mL) was added to it and stirred overnight. The precipitate formed was filtered and treated with sodium

hydroxide (10 %, 30 mL) solution and stirred at room temperature for 2h. Acidification with 5N HCl (25 mL)

yielded 16 in 87-95 % yield as shown in Table 2. To a solution of anthracenethiols 16 (5 mmol) dissolved in

chloroform (20 ml), KOH (0.20 g, 5 mmol) dissolved in methanol was added at 0 o C followed by propargyl

bromide (0.38 mL, 5 mmol) and stirred overnight. Reaction mixture was concentrated, washed with water and

extracted with dichloromethane to obtain thioethers 17 in 75-85 % yields. Thioethers 17 were purified by silica

gel column chromatography using a mixture of hexane and dichloromethane as eluents. IMDA reaction of 17

(5 mmol) was effected by refluxing in p-xylene (10 mL) (5-10h) to obtain corresponding barrelenes 6 in 70-80

% yields after recrystallization from suitable solvents.

Table 2. Amounts and yields of formation of intermediates 14, 16 and 17

Synthesis of tethered sulfone 7. Tethered barrelene 6a (200 mg, 0.76 mmol) was dissolved in DMF (5 mL) and stirred with hydrogen peroxide (30 %, 2 mL) and boric acid (0.006 g, 0.1 mmol) for 12h to obtain the

corresponding sulfone 7 (78 %).

General procedure for the synthesis of tethered ethers 8. Aldehydes 9 (16 mmol) were reduced to

anthracene methanols 14 using sodium borohydride (1.1 g, 30 mmol) dissolved in methanol.

Anthracenemethanols 14 (10 mmol) were converted to the corresponding sodium salts 18 by treating with

sodium hydride (0.48 g, 20 mmol) in THF. Propargyl bromide was added to it and stirred at room temperature

for 2h followed by refluxing in THF for 4h to obtain 19 (75-85 % yield, Table 3). Propargyl ethers 19 (5 mmol)

were refluxed in p-xylene (10 mL) (12 h to 20 h) to obtain the corresponding barrelenes 8 (80-90 %). The

products were purified by silica gel column chromatography using a mixture of hexane and dichloromethane

as eluents followed by recrystallization from suitable solvents and structures were confirmed by spectral and

analytical data.

Table 3. Amounts and yields of formation of intermediate 19

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