scholarly journals The regioselective dehydration of unsymmetrical secondary alcohols under Mitsunobu's reaction conditions.

1990 ◽  
Vol 38 (9) ◽  
pp. 2377-2380 ◽  
Author(s):  
Hiroyuki AKITA ◽  
Harutami YAMADA ◽  
Hiroko MATSUKURA ◽  
Tadashi NAKATA ◽  
Takeshi OISHI
Keyword(s):  
Secondary Alcohols ◽  
Reaction Conditions

Kinetics and Mechanism of Oxidation of Aliphatic Secondary Alcohols by Benzimidazolium Fluorochromate in Dimethyl Sulphoxide Solvent

2021 ◽  
Vol 37 (3) ◽  
pp. 626-633
Author(s):  
Bhawana Arora ◽  
Jitendra Ojha ◽  
Pallavi Mishra
Keyword(s):  
Activation Parameters ◽  
Sigmatropic Rearrangement ◽  
Dimethyl Sulphoxide ◽  
Secondary Alcohols ◽  
Hydrogen Ions ◽  
Reaction Conditions ◽  
First Order Kinetics ◽  
Aqueous Solvent ◽  
Ester Formation ◽  
Different Temperatures

Oxidation of secondary alcohols is an important part of synthetic organic chemistry. Various studies are carried out at different reaction conditions to determine the best mechanistic pathways. In our study, oxidation of different secondary alcohols was done by using Benzimidazolium Fluorochromate in Dimethyl Sulphoxide, which is a non-aqueous solvent. Oxidation resulted in the formation of ketonic compounds. The reaction showed first order kinetics both in BIFC and in the alcohols. Hydrogen ions were used to catalyze the reaction. We selected four different temperatures to carry out our study. The correlation within the activation parameters like enthalpies and entropies was in accordance with the Exnerʼs criterion. The deuterated benzhydrol (PhCDOHPh) oxidation exhibited an important primary kinetic isotopic effect (kH / kD = 5.76) at 298 K. The solvent effect was studied using the multiparametric equations of Taft and Swain. There was no effect of addition of acrylonitrile on the oxidation rate. The mechanism involved sigmatropic rearrangement with the transfer of hydrogen ion taking place from alcohol to the oxidant via a cyclic chromate ester formation.

N,O-ligated Pd(ii) complexes for catalytic alcohol oxidation

2014 ◽  
Vol 4 (8) ◽  
pp. 2526-2534 ◽  
Author(s):  
Laura M. Dornan ◽  
Gráinne M. A. Clendenning ◽  
Mateusz B. Pitak ◽  
Simon J. Coles ◽  
Mark J. Muldoon
Keyword(s):  
Crystal Structure ◽  
Sulfonic Acid ◽  
Active Catalyst ◽  
Alcohol Oxidation ◽  
Secondary Alcohols ◽  
Reaction Conditions ◽  
Highly Active

The (HSA)Pd(OAc)2 complex (where HSA = 8-hydroxyquinoline-2-sulfonic acid) is a highly active catalyst for the oxidation of a range of secondary alcohols in 4–6 hours at a low loading of 0.5 mol%. The crystal structure has been obtained and the influence of reaction conditions on catalyst degradation was also examined.

scholarly journals Iridium Catalyzed Synthesis of Tetrahydro-1H-Indoles by Dehydrogenative Condensation

Inorganics ◽  
2019 ◽  
Vol 7 (8) ◽  
pp. 97 ◽  
Author(s):  
Forberg ◽  
Kallmeier ◽  
Kempe
Keyword(s):  
Title Compound ◽  
Secondary Alcohols ◽  
Pd Catalyst ◽  
Pincer Ligand ◽  
Reaction Conditions ◽  
Iridium Catalyst ◽  
Synthetic Procedure ◽  
Reaction Proceeds ◽  
Synthetic Routes ◽  
First Time

Novel synthetic routes to the commonly encountered indole motif are highly sought after. Tetrahydro-1H-indoles were synthesized for the first time from secondary alcohols and 2aminocyclohexanol in the presence of a well-established iridium catalyst using a modified synthetic procedure recently developed for the synthesis of hydrocarbazoles. The catalyst is stabilized by an inexpensive and easy-to-synthesize triazine based PN5P pincer ligand. The reaction proceeds through acceptorless dehydrogenative condensation (ADC) and yields the title compound, dihydrogen, and water and can thus be classified as sustainable synthesis. Overall, five examples, three of which were previously unknown compounds, were prepared. The propitious isolated yields and the mild reaction conditions show the synthetic value of this approach. These tetrahydroindoles can be quantitatively dehydrogenated over a heterogeneous Pd catalyst to yield the corresponding indoles.

ChemInform Abstract: The Regioselective Dehydration of Unsymmetrical Secondary Alcohols Under Mitsunobu′s Reaction Conditions.

ChemInform ◽  
2010 ◽  
Vol 22 (18) ◽  
pp. no-no
Author(s):  
H. AKITA ◽  
H. YAMADA ◽  
H. MATSUKURA ◽  
T. NAKATA ◽  
T. OISHI
Keyword(s):  
Secondary Alcohols ◽  
Reaction Conditions

scholarly journals Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

2018 ◽  
Vol 14 ◽  
pp. 2090-2097 ◽  
Author(s):  
Jiao-Na Han ◽  
Cong Du ◽  
Xinju Zhu ◽  
Zheng-Long Wang ◽  
Yue Zhu ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Secondary Alcohols ◽  
Reaction Conditions ◽  
Biologically Relevant ◽  
Efficient Approach ◽  
Directing Group ◽  
Aryl Ethers

A cobalt-catalyzed C(sp2)–H alkoxylation of 1-naphthylamine derivatives has been disclosed, which represents an efficient approach to synthesize aryl ethers with broad functional group tolerance. It is noteworthy that secondary alcohols, such as hexafluoroisopropanol, isopropanol, isobutanol, and isopentanol, were well tolerated under the current catalytic system. Moreover, a series of biologically relevant fluorine-aryl ethers were easily obtained under mild reaction conditions after the removal of the directing group.

Advances in the Mitsunobu Reaction: An Excellent Organic Protocol with Versatile Applications

2019 ◽  
Vol 16 (2) ◽  
pp. 127-140 ◽  
Author(s):  
Sharad Kumar Panday
Keyword(s):  
Organic Synthesis ◽  
Turning Point ◽  
Mitsunobu Reaction ◽  
Present Review ◽  
Secondary Alcohols ◽  
Rapid Progress ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Basic Objective ◽  
Made In

The beginning of 1970’s may well be regarded as turning point in the area of organic synthesis when an efficient and straight forward strategy for the reaction of primary and/or secondary alcohols with variety of nucleophiles in the presence of triphenylphosphine and azodicarboxylate reagent was discovered by O. Mitsunobu and since then rapid progress has been made in understanding and applying the Mitsunobu reaction for various derivatization reactions. Due to versatile applications and mild reaction conditions associated with the said strategy, the Mitsunobu reaction has received much attention in the last almost fifty years and has been well reported. The basic objective of this review is to pay attention on the recent advances and applications of the Mitsunobu reaction particularly in last decade. The attention has also been paid to describe various modifications which have been explored in the traditional Mitsunobu reaction by substituting P (III) reagents or azodicarboxylate reagents with other suitable reagents or else using an organocatalyst with the objective to improve upon the traditional Mitsunobu reaction. In the present review we wish to report the major advancements achieved in last few years which are likely to be beneficial for the researchers across the globe.

Undecagold labeling of tRNA

1991 ◽  
Vol 49 ◽  
pp. 44-45
Author(s):  
James F. Hainfeld ◽  
Kyra M. Alford ◽  
Mathias Sprinzl ◽  
Valsan Mandiyan ◽  
Santa J. Tumminia ◽  
...  
Keyword(s):  
High Resolution ◽  
Transmission Electron Micrograph ◽  
Anticodon Loop ◽  
Electron Micrograph ◽  
Reaction Conditions ◽  
Scanning Transmission Electron ◽  
Transmission Electron ◽  
Scanning Transmission

The undecagold (Au11) cluster was used to covalently label tRNA molecules at two specific ribonucleotides, one at position 75, and one at position 32 near the anticodon loop. Two different Au11 derivatives were used, one with a monomaleimide and one with a monoiodacetamide to effect efficient reactions.The first tRNA labeled was yeast tRNAphe which had a 2-thiocytidine (s2C) enzymatically introduced at position 75. This was found to react with the iodoacetamide-Aun derivative (Fig. 1) but not the maleimide-Aun (Fig. 2). Reaction conditions were 37° for 16 hours. Addition of dimethylformamide (DMF) up to 70% made no improvement in the labeling yield. A high resolution scanning transmission electron micrograph (STEM) taken using the darkfield elastically scattered electrons is shown in Fig. 3.

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