The generation and properties of episulfonium intermediates. 8. Regioselectivity in the nucleophilic ring opening of episulfonium ion derivatives of some unsymmetrical alkyl- and arylolefins

1979 ◽  
Vol 28 (11) ◽  
pp. 2336-2340
Author(s):  
A. S. Gybin ◽  
V. A. Smit ◽  
V. S. Bogdanov ◽  
M. Z. Krimer
Keyword(s):  
Ring Opening ◽  
Derivatives Of ◽  
Nucleophilic Ring Opening ◽  
Episulfonium Ion

scholarly journals Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

ACS Omega ◽  
2018 ◽  
Vol 3 (12) ◽  
pp. 17562-17572 ◽  
Author(s):  
Gaurav Goswami ◽  
Navya Chauhan ◽  
Abhijit Mal ◽  
Subhomoy Das ◽  
Mowpriya Das ◽  
...  
Keyword(s):  
Ring Opening ◽  
Synthetic Route ◽  
Nucleophilic Ring Opening

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Stereochemistry of the nucleophilic ring-opening of activated bicyclo-[3.1.0]Hexanes.

1977 ◽  
Vol 18 (1) ◽  
pp. 109-112 ◽  
Author(s):  
Daiei Tunemoto ◽  
Nobuhiko Araki ◽  
Kiyosi Kondo
Keyword(s):  
Ring Opening ◽  
Nucleophilic Ring Opening

A Telluride-Triggered Nucleophilic Ring Opening of Monoactivated Cyclopropanes1

2004 ◽  
Vol 6 (13) ◽  
pp. 2225-2228 ◽  
Author(s):  
Dmitry V. Avilov ◽  
Mahesh G. Malusare ◽  
Engin Arslancan ◽  
Donald C. Dittmer
Keyword(s):  
Ring Opening ◽  
Nucleophilic Ring Opening

Derivatives of isatin in aqueous solution. I. Kinetics of ring opening of Isatin-5-sulfonate

1981 ◽  
Vol 34 (2) ◽  
pp. 365 ◽  
Author(s):  
H Stunzi
Keyword(s):  
Ring Opening ◽  
Rate Of Change ◽  
Spectroscopic Methods ◽  
Ph Values ◽  
Buffer Region ◽  
Pka Value ◽  
Back Titration ◽  
Kinetics Of ◽  
Derivatives Of ◽  
Sulfonate Anion

The reactions of isatin-5-sulfonate anion (si-) which cause a hysteresis in pH titrations were studied by pH-metric and n.m.r, spectroscopic methods. Rapid alkalimetric titrations [I 0.15 M (KNO3),37�] gave the pKa value corresponding to the addition of OH- to si- [pKa(ring) 9.55]. The slow ring opening to the sulfonatoisatate dianion (sia2-) led to a drift of the pH values towards an equilibrium buffer region. Its pKa, value [pKa(eq) 3.44] corresponds to the reaction si-+H2O ↔ sia 2-+H+ Rapid back-titration gave the pKa value of the ring-opened species Hsia- [pKa(open) c. 1.3]. The rate law for the ring opening d[sia]/dt=k2 [siOH](OH)+k1*[si] was obtained from the rate of change of pH. N-Methylisatin-5-sulfonate behaves analogously.

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