ChemInform Abstract: An Unexpected Migration of O-Silyl Group under Mitsunobu Reaction Conditions.

ChemInform ◽  
2011 ◽  
Vol 42 (38) ◽  
pp. no-no
Author(s):  
Ramu Sridhar Perali ◽  
Suresh Mandava ◽  
Venkata Rao Chunduri
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Silyl Group

An unexpected migration of O-silyl group under Mitsunobu reaction conditions

2011 ◽  
Vol 52 (23) ◽  
pp. 3045-3047 ◽  
Author(s):  
Ramu Sridhar Perali ◽  
Suresh Mandava ◽  
Venkata Rao Chunduri
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Silyl Group

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.

Nucleosteroids: Synthesis of Purinyl-Steroid Derivatives under Mitsunobu Reaction Conditions.

ChemInform ◽  
2005 ◽  
Vol 36 (27) ◽  
Author(s):  
Raul A. Cadenas ◽  
Maria E. Gelpi ◽  
Jorge Mosettig
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions

Synthesise of (4-Ethynyl-Phenyl)-(4-trifluoromethyl-phenyl)-Diazene, a Novel Intermediate of Azobenzene Liquid Crystal with High Birefrigence

2014 ◽  
Vol 584-586 ◽  
pp. 1705-1708
Author(s):  
Xiao Ping Huo ◽  
Qi Pei Xu ◽  
Zong Cheng Miao
Keyword(s):  
Liquid Crystal ◽  
Raw Materials ◽  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Target Compound ◽  
Reaction Conditions ◽  
Silyl Group ◽  
Sonogashira Coupling Reaction ◽  
Optimum Reaction ◽  
Ft Ir

In order to obtain an important azobenzene liquid crystal intermediate with phenylacetylene group, Sonogashira coupling reaction was used to preparation the compound. In this paper, the intermediate was synthesized by (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene (TMSA) as raw materials, and then the trimethyl silyl group was removaled under the action of K2CO3. During the synthesis, the optimum reaction conditions were obtained, that the mol ratio of (4-Iodo-phenyl)-(4-trifluoromethyl-phenyl)-diazene and trimethyl silyl acetylene was 1:2, the reaction temperature was 80 oC. Fourier transform infrared spectroscopy (FT-IR) was used to measure the molecular structure of the target compound.

Regiospecific O-alkylation of δ-tetronic acids under mitsunobu-reaction conditions

1990 ◽  
Vol 31 (48) ◽  
pp. 6973-6976 ◽  
Author(s):  
Joginder S Bajwa ◽  
Robert C Anderson
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions

Oxidations of some α-amino acids under mitsunobu reaction conditions

1988 ◽  
Vol 29 (37) ◽  
pp. 4661-4664 ◽  
Author(s):  
Teodozyj Kolasa ◽  
Marvin J. Miller
Keyword(s):  
Amino Acids ◽  
Mitsunobu Reaction ◽  
Reaction Conditions

Introduction of a substituent at the 5″-position of N-Boc neomycin B under Mitsunobu reaction conditions

2005 ◽  
Vol 3 (11) ◽  
pp. 2064 ◽  
Author(s):  
Angelica Hernandez Linares ◽  
Dominique Fourmy ◽  
Jean-Louis Fourrey ◽  
Ali Loukaci
Keyword(s):  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Neomycin B

scholarly journals Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

2021 ◽  
Vol 17 ◽  
pp. 2642-2649
Author(s):  
Akhil K Dubey ◽  
Raghunath Chowdhury
Keyword(s):  
Temperature Control ◽  
Carbonyl Compounds ◽  
Room Temperature ◽  
Conjugate Addition ◽  
High Reactivity ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Silyl Group ◽  
Solvent Free Conditions ◽  
Solvent Free Synthesis

An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.

Sign in / Sign up

Export Citation Format

Share Document