1992
DOI: 10.1002/cber.19921250508
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Dithiocarbonsäuren und Derivate aus Carbonsäureestern und Lactonen mit dem Organoborsulfid‐Reagenz (9‐BBN)2S

Abstract: Bis( 1,5-cyclooctanediylboryl) sulfide (1) reacts with carboxylic esters to give the dithiocarboxylic 1,5-cyclooctanediylboryl esters 2a-f in high yields (2a: X-ray crystal structure analysis). Methanolysis of 2a -f leads to the dithiocarboxylic acids (9-BBN)zS 5a -f, which form the corresponding piperidinium salts in the presence of piperidine. When cyclic esters (y-, 6-lactones) are allowed to react with 1, the boryloxy-substituted dithiocarboxylic 1,5-cyclooctanediylboryl esters 3a -c are obtained. Dithioca… Show more

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Cited by 10 publications
(2 citation statements)
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“…Phosphorus pentasulfide [17][18][19], 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) [20,21], boron sulfide [22,23], and bis (9-borabicyclo[3.3.1]non-9-yl) sulfide [24] have served as thionylation agents in this reaction. We employed Lawesson's reagent [25] for thionylation of the exocyclic oxygen atom.…”
mentioning
confidence: 99%
“…Phosphorus pentasulfide [17][18][19], 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) [20,21], boron sulfide [22,23], and bis (9-borabicyclo[3.3.1]non-9-yl) sulfide [24] have served as thionylation agents in this reaction. We employed Lawesson's reagent [25] for thionylation of the exocyclic oxygen atom.…”
mentioning
confidence: 99%
“…D er bifunktionelle B-Organorest ist Austausch-stabil, so daß bei (9-BBN)2ElVI-Verbindungen die Bildung von Monoorganodichalkogenoboranen unterbleibt. Bis(l,5-cyclooctandiylboryl)sulfide [4] und -selenide [5] eig nen sich daher in übersichtlich verlaufenden R eaktionen als Reagenzien zur Übertragung von Schwefel [4,6] bzw. Selen [5,7] auf organische sowie andere Elem ent-Verbindungen [4,5].…”
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