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A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β‐Mercaptoalcohols with Fluorinated α‐Bromoenones


Obijalska, Emilia; Pawelec, Maria; Mloston, Grzegorz; Capperucci, Antonella; Tanini, Damiano; Heimgartner, Heinz (2018). A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β‐Mercaptoalcohols with Fluorinated α‐Bromoenones. European Journal of Organic Chemistry, 2018(27-28):3716-3723.

Abstract

Isomeric fluorinated α‐bromoenones react with dinucleophilic β‐mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S‐heterocycles or non‐cyclic products were obtained. With 3‐bromo‐1,1,1‐trifluorobut‐3‐en‐2‐ones derivatives of 1,4‐oxathianes were formed, but isomeric 2‐bromo‐4,4,4‐trifluorobut‐2‐en‐1‐ones yielded 1,3‐oxathiolanes or non‐cyclic sulfides. The thia‐Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.

Abstract

Isomeric fluorinated α‐bromoenones react with dinucleophilic β‐mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S‐heterocycles or non‐cyclic products were obtained. With 3‐bromo‐1,1,1‐trifluorobut‐3‐en‐2‐ones derivatives of 1,4‐oxathianes were formed, but isomeric 2‐bromo‐4,4,4‐trifluorobut‐2‐en‐1‐ones yielded 1,3‐oxathiolanes or non‐cyclic sulfides. The thia‐Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.

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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
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry
Language:English
Date:April 2018
Deposited On:10 Apr 2018 12:42
Last Modified:19 Aug 2018 15:25
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1099-0690
Funders:National Science Center (Cracow, Poland) Opus-7 Project (Grant 2014/13/B/ST5/04004
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/ejoc.201701752

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