Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent:  Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom Substituents

Leticia Ayala; Claudia G. Lucero; Jan Antoinette C. Romero; Sarah A. Tabacco; K. A. Woerpel

doi:10.1021/ja037935a

Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent: Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom Substituents

Journal of the American Chemical Society ◽

10.1021/ja037935a ◽

2003 ◽

Vol 125 (50) ◽

pp. 15521-15528 ◽

Cited By ~ 181

Author(s):

Leticia Ayala ◽

Claudia G. Lucero ◽

Jan Antoinette C. Romero ◽

Sarah A. Tabacco ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Electrostatic Stabilization ◽

Oxocarbenium Ions

Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent: Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom Substituents.

ChemInform ◽

10.1002/chin.200417126 ◽

2004 ◽

Vol 35 (17) ◽

Author(s):

Leticia Ayala ◽

Claudia G. Lucero ◽

Jan Antoinette C. Romero ◽

Sarah A. Tabacco ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Electrostatic Stabilization ◽

Oxocarbenium Ions

ChemInform Abstract: Nucleophilic Substitution Reactions of 2-Phenylthio-Substituted Carbohydrate Acetals and Related Systems: Episulfonium Ions vs. Oxocarbenium Ions as Reactive Intermediates

ChemInform ◽

10.1002/chin.200822229 ◽

2008 ◽

Vol 39 (22) ◽

Author(s):

Matthew G. Beaver ◽

Susan B. Billings ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Reactive Intermediates ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers

Journal of the American Chemical Society ◽

10.1021/ja993366o ◽

2000 ◽

Vol 122 (1) ◽

pp. 168-169 ◽

Cited By ~ 138

Author(s):

Jan Antoinette C. Romero ◽

Sarah A. Tabacco ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

ChemInform Abstract: Diastereoselective Nucleophilic Substitution Reactions of Oxasilacyclopentane Acetals: Application of the “Inside Attack” Model for Reactions of Five-Membered Ring Oxocarbenium Ions.

ChemInform ◽

10.1002/chin.200237175 ◽

2010 ◽

Vol 33 (37) ◽

pp. no-no

Author(s):

Teresa J. Bear ◽

Jared T. Shaw ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Attack Model ◽

Oxocarbenium Ions

Nucleophilic Substitution Reactions of 2-Phenylthio-Substituted Carbohydrate Acetals and Related Systems: Episulfonium Ions vs. Oxocarbenium Ions as Reactive Intermediates

European Journal of Organic Chemistry ◽

10.1002/ejoc.200700911 ◽

2008 ◽

Vol 2008 (5) ◽

pp. 771-781 ◽

Cited By ~ 29

Author(s):

Matthew G. Beaver ◽

Susan B. Billings ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Reactive Intermediates ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

Diastereoselective Nucleophilic Substitution Reactions of Oxasilacyclopentane Acetals: Application of the “Inside Attack” Model for Reactions of Five-Membered Ring Oxocarbenium Ions

The Journal of Organic Chemistry ◽

10.1021/jo010823m ◽

2002 ◽

Vol 67 (7) ◽

pp. 2056-2064 ◽

Cited By ~ 11

Author(s):

Teresa J. Bear ◽

Jared T. Shaw ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Attack Model ◽

Oxocarbenium Ions

Using Nucleophilic Substitution Reactions to Understand How a Remote Alkyl or Alkoxy Substituent Influences the Conformation of Eight-Membered Ring Oxocarbenium Ions

Organic Letters ◽

10.1021/ol047998d ◽

2004 ◽

Vol 6 (25) ◽

pp. 4739-4741 ◽

Cited By ~ 13

Author(s):

Stephen Chamberland ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

ChemInform Abstract: Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions Through Pseudoaxial Conformers.

ChemInform ◽

10.1002/chin.200015123 ◽

2010 ◽

Vol 31 (15) ◽

pp. no-no

Author(s):

Jan Antoinette C. Romero ◽

Sarah A. Tabacco ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

Synthesis of Diastereomeric Pyrrolidine Sulfamides via Anchimerically Assisted Nucleophilic Substitution Reactions

Letters in Organic Chemistry ◽

10.2174/1570178615666180110162202 ◽

2018 ◽

Vol 15 (5) ◽

pp. 352-358

Author(s):

Jorge Vargas-Caporali ◽

Arie van der Lee ◽

Georges Dewynter ◽

Eusebio Juaristi

Keyword(s):

Nucleophilic Substitution ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions

The unexpected reactivity of 9-iodo-nido-carborane: from nucleophilic substitution reactions to the synthesis of tricobalt tris(dicarbollide) Na[4,4′,4′′-(MeOCH2CH2O)3-3,3′,3′′-Co3(μ3-O)(μ3-S)(1,2-C2B9H10)3]

Dalton Transactions ◽

10.1039/d0dt03857a ◽

2021 ◽

Vol 50 (7) ◽

pp. 2671-2688

Author(s):

Marina Yu. Stogniy ◽

Sergey A. Anufriev ◽

Akim V. Shmal'ko ◽

Sergey M. Antropov ◽

Aleksei A. Anisimov ◽

...

Keyword(s):

Nucleophilic Substitution ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions

An unusual reactivity of 9-iodo-nido-carborane [9-I-7,8-C2B9H11]− towards nucleophiles under strong basic conditions was revealed.