Literature DB >> 26728333

Ammonium catalyzed cyclitive additions: evidence for a cation-π interaction with alkynes.

Edith Nagy1, Elijah St Germain1, Patrick Cosme1, Pradip Maity1, Andrew C Terentis1, Salvatore D Lepore1.   

Abstract

The addition of carbamate nitrogen to a non-conjugated carbon-carbon triple bond is catalyzed by an ammonium salt leading to a cyclic product. Studies in homogeneous systems suggest that the ammonium agent facilitates nitrogen-carbon bond formation through a cation-π interaction with the alkyne unit that, for the first time, is directly observed by Raman spectroscopy.

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Year:  2016        PMID： 26728333      PMCID： PMC4732893          DOI： 10.1039/c5cc08641h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  20 in total

1.  The Cationminus signpi Interaction.

Authors:  Jennifer C. Ma; Dennis A. Dougherty
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

2.  Solution complexation between potassium iodide and lariat ethers having pi-donor sidearms.

Authors:  Jiaxin Hu; George W Gokel
Journal:  Chem Commun (Camb)       Date:  2003-10-21       Impact factor: 6.222

Review 3.  Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

4.  Aromatic transition states in nonpericyclic reactions: anionic 5-endo cyclizations are aborted sigmatropic shifts.

Authors:  Kerry Gilmore; Mariappan Manoharan; Judy I-Chia Wu; Paul v R Schleyer; Igor V Alabugin
Journal:  J Am Chem Soc       Date:  2012-06-13       Impact factor: 15.419

5.  Intramolecular cation-pi interaction in organic synthesis.

Authors:  Shinji Yamada
Journal:  Org Biomol Chem       Date:  2007-08-02       Impact factor: 3.876

6.  UV resonance Raman study of cation-π interactions in an indole crown ether.

Authors:  Diana E Schlamadinger; Megan M Daschbach; George W Gokel; Judy E Kim
Journal:  J Raman Spectrosc       Date:  2011-04       Impact factor: 3.133

Review 7.  Cation-π interaction: its role and relevance in chemistry, biology, and material science.

Authors:  A Subha Mahadevi; G Narahari Sastry
Journal:  Chem Rev       Date:  2012-11-13       Impact factor: 60.622

8.  Catalytic synthesis of nonracemic azaproline derivatives by cyclization of β-alkynyl hydrazines under kinetic resolution conditions.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-15       Impact factor: 15.336

9.  Cu(I) recognition via cation-pi and methionine interactions in CusF.

Authors:  Yi Xue; Anna V Davis; Gurusamy Balakrishnan; Jay P Stasser; Benjamin M Staehlin; Pamela Focia; Thomas G Spiro; James E Penner-Hahn; Thomas V O'Halloran
Journal:  Nat Chem Biol       Date:  2007-12-23       Impact factor: 15.040

10.  Pentakis(trifluoromethyl)phenyl, a sterically crowded and electron-withdrawing group: synthesis and acidity of pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline.

Authors:  Agnes Kütt; Valeria Movchun; Toomas Rodima; Timo Dansauer; Eduard B Rusanov; Ivo Leito; Ivari Kaljurand; Juta Koppel; Viljar Pihl; Ivar Koppel; Gea Ovsjannikov; Lauri Toom; Masaaki Mishima; Maurice Medebielle; Enno Lork; Gerd-Volker Röschenthaler; Ilmar A Koppel; Alexander A Kolomeitsev
Journal:  J Org Chem       Date:  2008-03-07       Impact factor: 4.354
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  1 in total

1.  A Teaching Experiment to Elucidate a Cation-π Effect in an Alkyne Cycloaddition Reaction and Illustrate Hypothesis Driven Design of Experiments.

Authors:  Elijah J St Germain; Andrew S Horowitz; Dominic Rucco; Evonne M Rezler; Salvatore D Lepore
Journal:  J Chem Educ       Date:  2016-12-22       Impact factor: 2.979
  1 in total

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