ChemInform Abstract: α‐PHENYLPROPIONIC ACID DERIVATIVES. SYNTHESIS AND DETHIATION OF 5‐BENZOYLBENZO(B)THIOPHENE‐3‐CARBOXYLIC ACID

Hannoun, Mohammad; BLAZEVIC, N.; Kolbah, D.; Mihalić, Mladen; Kajfež, F.

doi:10.1002/chin.198319188

Cited by 4 publications

(4 citation statements)

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“…1 Acid-mediated displacement of aryls by benzene is also known to occur in the isolation of diphenylmethane from the alkylation of benzene by substituted arylmethanols 8 and substituted benzyl halides. [9][10][11][12][13][14] In addition, there are two reports of acid-mediated aryl-benzene exchange with diarylmethanes. 8,9 Next we explored the reactions of other substituted azetidinones.…”

Section: Resultsmentioning

confidence: 99%

The acid-mediated ring opening reactions of α-aryl-lactams

King

Caddick

2012

Org. Biomol. Chem.

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4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl exchange. Lactams of ring size 7 and higher also ring open, but only 7- and 8-membered rings give pure diphenylalkylamides. AlCl(3) only ring opens the 4-aryl-azetidinones.

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Section: Resultsmentioning

confidence: 99%

The acid-mediated ring opening reactions of α-aryl-lactams

King

Caddick

2012

Org. Biomol. Chem.

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“…Benzothiophene-2,3-dione and benzothiophene-2,3-dicarboxylic acid anhydride were synthesized according to the procedure of Papa et al . and Hannoun et al Diazomethane was prepared from diazald (Aldrich Chemical Co. Inc.) by hydrolysis using 30% KOH aqueous solution, and the product was collected in cooled diethyl ether.…”

Section: Methodsmentioning

confidence: 99%

Identification of Desulfurization Products in the Photochemical Desulfurization Process for Benzothiophenes and Dibenzothiophenes from Light Oil Using an Organic Two-Phase Extraction System

Shiraishi

Hirai

Komasawa

1999

Ind. Eng. Chem. Res.

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The desulfurization products of benzothiophenes (BTs) and dibenzothiophenes (DBTs), produced during a new photochemical desulfurization process, employing an organic two-phase liquidliquid extraction system, have been identified. The acidic products were converted to their corresponding methyl esters by reaction with diazomethane and were then analyzed. In acetonitrile, BT is converted first to benzothiophene-2,3-dione, followed by hydrolysis, loss of carbon monoxide, and oxidation of the sulfur atom, to be converted finally to 2-sulfobenzoic acid. 3-Methyl BT and 2,3-dimethyl BT produce 2-sulfobenzoic acid and two other products, benzenesulfonic acid and 2-acetylbenzenesulfonic acid. DBT is first photooxidized to DBT sulfoxide, which is then further oxidized to form DBT sulfone or dibenz[c,e][1,2]oxathiin-6-oxide. The latter is then oxidized and finally converted to 2-sulfobenzoic acid via dibenz[c,e][1,2]oxathiin-6,6-dioxide. Benzothiophene-2,3-dicarboxylic acid is likely to be formed directly by the oxidation of DBT by a singlet oxygen, generated by photosensitization with DBT sulfone. 4-Methyl DBT and 4,6-dimethyl DBT finally produce the corresponding sulfobenzoic acid, dicarboxylic acid, and sulfone. The yields of these products are seriously affected by the presence of methyl substituents.

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“…Sulfones of 7-MBT and 2,3-MBT were synthesized (14). 5-Methylbenzothiophene-2,3-dione and 7-methylbenzothiophene-2,3-dione were also synthesized (15). m-Tolyl methyl sulfoxide and m-tolyl methyl sulfone were prepared according to the procedures of Cerniani and Modena (16).…”

Section: Introductionmentioning

confidence: 99%

Diones, sulfoxides, and sulfones from the aerobic cometabolism of methylbenzothiophenes by Pseudomonas strain BT1

Saftic¹,

Fedorak²,

Andersson³

1992

Environ. Sci. Technol.

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ChemInform Abstract: α‐PHENYLPROPIONIC ACID DERIVATIVES. SYNTHESIS AND DETHIATION OF 5‐BENZOYLBENZO(B)THIOPHENE‐3‐CARBOXYLIC ACID

Abstract: p‐Thiokresol (I) kondensiert mit Oxalylchlorid zum Dioxo‐benzothiophen (II), das mit Chloressigsäure zur Dicarbonsäure (IIIa) führt, die zu (IIIb) decarboxyliert werden kann.

Cited by 4 publications

References 1 publication

The acid-mediated ring opening reactions of α-aryl-lactams

The acid-mediated ring opening reactions of α-aryl-lactams

Identification of Desulfurization Products in the Photochemical Desulfurization Process for Benzothiophenes and Dibenzothiophenes from Light Oil Using an Organic Two-Phase Extraction System

Diones, sulfoxides, and sulfones from the aerobic cometabolism of methylbenzothiophenes by Pseudomonas strain BT1

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