St. John's, Canada
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Deslongchamps G.,University of New Brunswick | Deslongchamps P.,OmegaChem Inc. | Deslongchamps P.,Laval University
Organic and Biomolecular Chemistry | Year: 2011

By taking into consideration bent bonds (τ-bonds, tau-bonds), the antiperiplanar hypothesis, the classic theory of resonance, and the preference for staggered bonds over eclipsed bonds in tetrahedral systems, a simple qualitative model is presented to rationalize the conformation and reactivity for a wide range of compounds containing double bonds and/or carbonyl groups. Alkenes, carbonyl and carboxyl derivatives, conjugated systems as well as other functional groups are revisited. This also leads to a simple model to understand aromaticity, and electrocyclic reactions. The bent bond model and the antiperiplanar hypothesis provide a qualitative model for better understanding the electron delocalization and the reactivity inherent to unsaturated organic systems by an alternative view of the classic resonance theory. © 2011 The Royal Society of Chemistry.


Mahe O.,Laval University | L'Heureux A.,OmegaChem Inc. | Couturier M.,OmegaChem Inc. | Bennett C.,Manchester Business Park | And 4 more authors.
Journal of Fluorine Chemistry | Year: 2013

The synthesis of N,N-disubstituted aminodifluorosulfinium tetrafluoroborate salts is reported, and their behavior as deoxofluorinating agent was evaluated. The deoxofluorination reactions were performed using a primary alcohol, a secondary alcohol and a ketone. Results show that subtle modification of the structure of the reagents can noticeably affect the reactivity and the selectivity in deoxofluorination reactions. © 2013 Elsevier B.V. All rights reserved.


Lheureux A.,OmegaChem Inc. | Beaulieu F.,OmegaChem Inc. | Bennett C.,Manchester Business Park | Bill D.R.,Pfizer | And 6 more authors.
Journal of Organic Chemistry | Year: 2010

Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-HF and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et3N3HF, Et3N2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products. © 2010 American Chemical Society.


Deslongchamps G.,University of New Brunswick | Deslongchamps P.,Laval University | Deslongchamps P.,OmegaChem Inc.
Organic and Biomolecular Chemistry | Year: 2016

The bent bond/antiperiplanar (BBA) hypothesis has been applied to the analysis of [1,3]-sigmatropic alkyl shifts. These thermal rearrangements, for which there is evidence that they proceed through diradical intermediates, can be interpreted by considering their transient allyl radical structures. For the thermolysis of cyclic molecules, the preferred generation of pyramidal allyl radicals in staggered conformations is postulated on the basis of the BBA hypothesis. This accounts for the preference of suprafacial rearrangement pathways as well as the extent of inversion or retention of configuration at the migrating carbons. © 2016 The Royal Society of Chemistry.


The invention relates to disubstituted-aminodifluorosulfinium salts represented by the formula (I). Processes for preparing same and methods of use as deoxofluorinating reagent is also provided.


Trademark
OmegaChem Inc. | Date: 2010-07-20

Reagent used to fluorinate other chemical compounds, for manufacturing other products.


Trademark
OmegaChem Inc. | Date: 2010-07-20

Reagent used to fluorinate other chemical compounds, for manufacturing other products.


PubMed | OmegaChem Inc.
Type: Journal Article | Journal: The Journal of organic chemistry | Year: 2010

Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-HF and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et(3)N.3HF, Et(3)N.2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.

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