25236-65-1Relevant articles and documents
Conformational Equilibria due to Ring Inversion in N-Alkyl-cis-decahydroisoquinolines
Bailey, Judith M.,Booth, Harold,Al-Shirayda, Hatif A. R. Y.
, p. 583 - 588 (1984)
The position of conformational equilibria due to ring inversion in N-alkyl-cis-decahydroisoquinolines (alkyl = Me, Et, Pri, CH2CF3, or CH2CCl3) has been assessed directly from 13C and/or 19F n.m.r. spectra recorded at temperatures between 173 and 253 K.The measured equilibrium constants are related to the inductive effect of the N-substituent which produces an increase (Me, Et, Pri) or decrease (CH2CF3, CH2CCl3) in the magnitude of the gauche propylamine-type repulsive interaction. 13C Chemical shifts are tabulated for the carbon atoms of the two twin-chair conformations undergoing exchange.
Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors
Górski, Bartosz,Basiak, Dariusz,Talko, Alicja,Basak, Tymoteusz,Mazurek, Tomasz,Barbasiewicz, Micha?
supporting information, p. 1774 - 1784 (2018/04/27)
Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.
Fluorinated organic azides-their preparation and synthetic applications
Tomaszewska, Joanna,Koroniak-Szejn, Katarzyna,Koroniak, Henryk
, p. 421 - 432 (2017/03/09)
Alkyl azides are widely used in many reactions. Although synthesis of such species is relatively well documented, fluorinated azides, especially with large perfluorinated or highly fluorinated groups, are sometimes tricky to make. The presence of fluorine in reacting molecules, sometimes causes significant changes in the reactivity of reacting species. In this paper we give a short overview of re-examination of currently available methods of synthesis of selected azides with highly fluorinated groups.
A method of hydroxylation org. compd. sulfonylated
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Page 21-22, (2010/02/14)
The invention concerns a method for sulphonylating a hydroxylated organic compound. The invention concerns in particular aliphatic hydroxylated compounds and more particularly those which comprise on their aliphatic chain, an electroattractive group. The
Method for sulphonylating a hydroxylated organic compound
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Page 8, (2010/11/30)
The invention concerns a method for sulphonylating a hydroxylated organic compound. The invention concerns in particular aliphatic hydroxylated compounds and more particularly those which comprise on their aliphatic chain, an electroattractive group. The
