Liquid Ammonia as a Dipolar Aprotic Solvent for Aliphatic Nucleophilic Substitution Reactions

2011 ◽  
Vol 76 (5) ◽  
pp. 1425-1435 ◽  
Author(s):  
Pengju Ji ◽  
John Atherton ◽  
Michael I. Page
Keyword(s):  
Nucleophilic Substitution ◽  
Liquid Ammonia ◽  
Aprotic Solvent ◽  
Substitution Reactions ◽  
Dipolar Aprotic Solvent ◽  
Nucleophilic Substitution Reactions

Aromatic radical nucleophilic substitution reactions initiated by sodium amalgam in liquid ammonia

1991 ◽  
Vol 56 (14) ◽  
pp. 4486-4489 ◽  
Author(s):  
Eduardo Austin ◽  
Ruben A. Alonso ◽  
Roberto A. Rossi
Keyword(s):  
Nucleophilic Substitution ◽  
Liquid Ammonia ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Aromatic Radical ◽  
Sodium Amalgam

The Kinetics and Mechanisms of Aromatic Nucleophilic Substitution Reactions in Liquid Ammonia

2011 ◽  
Vol 76 (9) ◽  
pp. 3286-3295 ◽  
Author(s):  
Pengju Ji ◽  
John H. Atherton ◽  
Michael I. Page
Keyword(s):  
Nucleophilic Substitution ◽  
Liquid Ammonia ◽  
Substitution Reactions ◽  
Aromatic Nucleophilic Substitution ◽  
Nucleophilic Substitution Reactions

scholarly journals Medium effect on the α-effect for nucleophilic substitution reactions of p-nitrophenyl acetate with benzohydroxamates and m-chlorophenoxide in DMSO–H2O mixtures as contrasts with MeCN–H2O mixtures: comparing two very different polar aprotic solvent components

2018 ◽  
Vol 96 (10) ◽  
pp. 922-928 ◽  
Author(s):  
Ik-Hwan Um ◽  
Hyun-Jung Moon ◽  
Young-Hee Shin ◽  
Julian M. Dust
Keyword(s):  
Nucleophilic Substitution ◽  
Aprotic Solvent ◽  
Reaction Medium ◽  
Hydroxamic Acids ◽  
Medium Effect ◽  
Substitution Reactions ◽  
Medium Effects ◽  
Nucleophilic Substitution Reactions ◽  
Polar Aprotic Solvent ◽  
Dipolar Aprotic Solvents

A kinetic study is reported on nucleophilic substitution reactions of p-nitrophenyl acetate (1a) with three α-effect nucleophiles, benzohydroxamate (BHA–), p-methylbenzohydroxamate (MBHA–), and p-methyl-N-methylbenzohydroxamate (M2BHA–), and a reference nucleophile, m-chlorophenoxide (m-ClPhO–), in DMSO–H2O mixtures of varying compositions at 25.0 ± 0.1 °C. Second-order rate constants for the reactions with BHA– and MBHA– decrease upon addition of DMSO to the reaction medium up to 60 mol % DMSO and then increase thereafter only a little. In contrast, M2BHA– and m-ClPhO– become much more reactive as the DMSO content in the medium increases. Such contrasting medium effects on reactivity are consistent with the report that hydroxamic acids behave as OH acids in H2O but as NH acids in dipolar aprotic solvents (e.g., DMSO and MeCN). It has been concluded that BHA– and MBHA– form an equilibrium of a reactive form I with less reactive species II in DMSO–H2O mixtures and the position of the equilibrium is dependent on solvent compositions. BHA– and MBHA– exhibit the α-effect in H2O but not in in 90 mol % DMSO. In contrast, the α-effect yielded by M2BHA– increases steeply up to 70 mol % DMSO and then levels off thereafter.

Synthesis of Diastereomeric Pyrrolidine Sulfamides via Anchimerically Assisted Nucleophilic Substitution Reactions

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]

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.

ChemInform Abstract: 2-AZATRIPTYCENE IN NUCLEOPHILIC SUBSTITUTION REACTIONS

1982 ◽  
Vol 13 (13) ◽  
Author(s):  
V. R. SKVARCHENKO ◽  
N. P. KOSHKINA
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions
Sign in / Sign up

Export Citation Format

Share Document