Trichloroisocyanuric acid (TCCA) and carboxamide interactions in TCCA/NaNO 2 triggered nitration of pyrrole and indole in aqueous aprotic media: A kinetic correlation of solvent properties with reactivity

2020 ◽  
Vol 53 (1) ◽  
pp. 164-186
Author(s):  
Govardhan Duguta ◽  
Bhooshan Muddam ◽  
Chinna Rajanna Kamatala ◽  
Umesh Kumar Utkoor
Keyword(s):  
Trichloroisocyanuric Acid ◽  
Solvent Properties

N-Chlorinative Ring Contraction of 1,4-Dimethoxyphthalazines via a Bicyclization/Ring-Opening Mechanism

Synthesis ◽  
2020 ◽  
Author(s):  
Jeong Kyun Im ◽  
Ilju Jeong ◽  
Jun-Ho Choi ◽  
Won-jin Chung ◽  
ByeongDo Yang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Reaction Conditions ◽  
Ring Contraction ◽  
Silyl Group ◽  
Favorskii Rearrangement ◽  
Mechanistic Analysis ◽  
Group A ◽  
Overall Efficiency ◽  
Trichloroisocyanuric Acid

AbstractAn unprecedented N-chlorinative ring contraction of 1,2-diazines was discovered and investigated with an electrophilic chlorinating reagent, trichloroisocyanuric acid (TCICA). Through optimization and mechanistic analysis, the assisting role of n-Bu4NCl as an exogenous nucleophile was identified, and the optimized reaction conditions were applied to a range of 1,4-dimethoxyphthalazine derivatives. Also, an improvement of overall efficiency was demonstrated by the use of a labile O-silyl group. A bicyclization/ring-opening mechanism, inspired by the Favorskii rearrangement, was proposed and supported by the DFT calculations. Furthermore, the efforts on scope expansion as well as the evaluation of other electrophilic promoters revealed that the newly developed ring contraction reactivity is a unique characteristic of 1,4-dimethoxyphthalazine scaffold and TCICA.

Do Ion Tethered Functional Groups Affect IL Solvent Properties? The Case of Sulfoxides and Sulfones.

ChemInform ◽  
2006 ◽  
Vol 37 (24) ◽  
Author(s):  
Nawal K. Sharma ◽  
Morgan D. Tickell ◽  
Jared L. Anderson ◽  
Joel Kaar ◽  
Veronica Pino ◽  
...  
Keyword(s):  
Functional Groups ◽  
Solvent Properties

Mild one-pot conversion of carboxylic acids to amides or esters with Ph3P/trichloroisocyanuric acid

2005 ◽  
Vol 46 (35) ◽  
pp. 5945-5947 ◽  
Author(s):  
Rogério da C. Rodrigues ◽  
Igor M.A. Barros ◽  
Edson L.S. Lima
Keyword(s):  
Carboxylic Acids ◽  
One Pot ◽  
Trichloroisocyanuric Acid

ChemInform Abstract: Trichloroisocyanuric Acid as a Novel and Versatile Reagent for the Rapid α-Thiocyanation of Ketones.

ChemInform ◽  
2012 ◽  
Vol 43 (9) ◽  
pp. no-no
Author(s):  
Shanshan Liu ◽  
Zhihao Guo ◽  
Yaqin Wang ◽  
Tianbao Wang ◽  
Liqiang Wu
Keyword(s):  
Trichloroisocyanuric Acid ◽  
Versatile Reagent

Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid

Synthesis ◽  
2016 ◽  
Vol 49 (07) ◽  
pp. 1648-1654
Author(s):  
Lúcia de Aguiar ◽  
Marcio de Mattos ◽  
Carlos Sanabria ◽  
Mariana do Casal ◽  
Raphael de Souza
Keyword(s):  
Trichloroisocyanuric Acid
Sign in / Sign up

Export Citation Format

Share Document