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Reactions of thioketones with dichlorocarbene


Mlostoń, Grzegorz; Romański, Jaroslaw; Swia̧tek, Anna; Heimgartner, Heinz (1999). Reactions of thioketones with dichlorocarbene. Helvetica Chimica Acta, 82:946-956.

Abstract

The reactions of sterically crowded cycloalkanethiones of type 2 with CHCl3/NaOH under phase-transfer catalysis (PTC) with benzyl(triethyl)ammonium chloride (TEBA) as catalyst afforded the corresponding 'gem.- dichlorothiiranes' of type 3 in good yields (cf. Scheme 2 and Table). The desulfurization, which, in some cases, occurred spontaneously, led to (dichloromethylidene)cycloalkanes of type 4. Similar results were obtained using Seyferth's reagent in boiling benzene. In the case of 2,2,6,6-tetramethylcyclohexanethione, reaction under PTC conditions after 3 h yielded only the corresponding dichloromethylidene derivative; on the other hand, workup after 1 h gave (2,2,6,6-tetramethylcyclohexylidene)methanethione (thioketene 9; Scheme 5).

Abstract

The reactions of sterically crowded cycloalkanethiones of type 2 with CHCl3/NaOH under phase-transfer catalysis (PTC) with benzyl(triethyl)ammonium chloride (TEBA) as catalyst afforded the corresponding 'gem.- dichlorothiiranes' of type 3 in good yields (cf. Scheme 2 and Table). The desulfurization, which, in some cases, occurred spontaneously, led to (dichloromethylidene)cycloalkanes of type 4. Similar results were obtained using Seyferth's reagent in boiling benzene. In the case of 2,2,6,6-tetramethylcyclohexanethione, reaction under PTC conditions after 3 h yielded only the corresponding dichloromethylidene derivative; on the other hand, workup after 1 h gave (2,2,6,6-tetramethylcyclohexylidene)methanethione (thioketene 9; Scheme 5).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Language:English
Date:1999
Deposited On:05 Nov 2013 16:40
Last Modified:30 Jul 2020 10:23
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Dr. Helmut Legerlotz Foundation, Universität Zürich
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/(SICI)1522-2675(19990609)82:6<946::AID-HLCA946>3.0.CO;2-P
Project Information:
  • : Funder
  • : Grant ID
  • : Project TitlePolish State Committee for Scientific Research
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel
  • : Funder
  • : Grant ID
  • : Project TitleDr. Helmut Legerlotz Foundation, Universität Zürich

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