Cleavage of 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)-2-phenyl-1,3-dithianes with HgO/BF3

Grün, E. and Wiegrebe, Wolfgang (1997) Cleavage of 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)-2-phenyl-1,3-dithianes with HgO/BF3. MONATSHEFTE FUR CHEMIE, 128 (10). pp. 1033-1049. ISSN 0026-9247, 1434-4475

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Abstract

The title compounds (5) were prepared by addition of 2-phenyl-1,3-dithiane anion (2-lithiated 10) to adequately substituted N-alkyl-3,4-dihydroisoquinolinium salts (7a-7g). Cleavage of compounds 5 with HgO/BF3 affords S-benzoyl-1,3-propanedithiol (4a) and the corresponding disulfide 4c, benzaldehyde, and Hg(I) ions. In contrast to the title compounds, 2-(alpha-dialkylaminobenzyl)-2-phenyl-1 ,3-dithianes (6) yield benzil under these conditions.

Item Type: Article
Uncontrolled Keywords: 1,3-DITHIOLENIUM SALTS; CARBONYL-COMPOUNDS; REAGENTS; DERIVATIVES; ALKALOIDS; TETRAHYDROISOQUINOLINES; 1,3-DITHIENIUM-SALT; ETHERS; 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)-2-phenyl-1,3-dithianes 2-(alpha-dialkylaminobenzyl)-2-phenyl-1,3-dithianes; cleavage with HgO/BF3; N-alkyl-3,4-dihydroisoquinolinium salts
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe
Depositing User: Dr. Gernot Deinzer
Date Deposited: 28 Mar 2023 09:08
Last Modified: 28 Mar 2023 09:08
URI: https://pred.uni-regensburg.de/id/eprint/50535

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