Direct C≡C Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into theo-Position of a Nitro Group on the Benzene Nucleus with Potassiumt-Butoxide inN,N-Dimethylformamide in the Air

1995 ◽  
Vol 68 (7) ◽  
pp. 2043-2051 ◽  
Author(s):  
Shuzo Akiyama ◽  
Kunihiko Tajima ◽  
Shin’ichi Nakatsuji ◽  
Kenichiro Nakashima ◽  
Kazuko Abiru ◽  
...  
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Triple Bond ◽  
Bond Formation ◽  
Benzene Nucleus ◽  
Direct Hydroxylation

scholarly journals Cathodic hydrodimerization of nitroolefins

2015 ◽  
Vol 11 ◽  
pp. 1163-1174 ◽  
Author(s):  
Michael Weßling ◽  
Hans J Schäfer
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Bond Formation ◽  
Cathodic Reduction ◽  
High Yield ◽  
Easy Access ◽  
Electrolysis Cell ◽  
Aldehydes And Ketones ◽  
Nef Reaction

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a ß,ß-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.

scholarly journals Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters

2017 ◽  
Vol 8 (9) ◽  
pp. 6686-6690 ◽  
Author(s):  
Abhijnan Ray Choudhury ◽  
Madhu Sudan Manna ◽  
Santanu Mukherjee
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Bond Formation ◽  
One Pot ◽  
Terminal Double Bond ◽  
Tertiary Center ◽  
Leaving Group

A formal umpolung strategy is presented for the enantioselective installation of an alkenyl group with a terminal double bond at a tertiary center. This one-pot two-step sequence relies on the unique features of the nitro group, which after inverting the polarity of the alkenylating agent toward the desired bond formation, itself serves as a leaving group.

ChemInform Abstract: Direct CC Triple Bond Formation from the CC Double Bond with Potassium tert-Butoxide in Dimethylformamide Containing Trace Amounts of Oxygen.

ChemInform ◽  
2010 ◽  
Vol 23 (10) ◽  
pp. no-no
Author(s):  
S. AKIYAMA ◽  
S. NAKATSUJI ◽  
K. NOMURA ◽  
K. MATSUDA ◽  
K. NAKASHIMA
Keyword(s):  
Double Bond ◽  
Triple Bond ◽  
Bond Formation

scholarly journals Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitro Group ◽  
Benzene Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Aromatic Rings ◽  
Compound C ◽  
The One

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

ChemInform Abstract: Chemistry of Organolanthanoids. Lanthanoid-Mediated C-C Bond Formation and Cleavage and C-C Double Bond Reduction.

ChemInform ◽  
1988 ◽  
Vol 19 (2) ◽  
Author(s):  
Z. HOU ◽  
Y. FUJIWARA ◽  
T. JINTOKU ◽  
N. MINE ◽  
K. YOKOO ◽  
...  
Keyword(s):  
Double Bond ◽  
Bond Formation

Critical Review of Biotransformational Studies on Steroids by Using Culture of Cunninghamella blakesleeana

2021 ◽  
Vol 18 ◽  
Author(s):  
Azizuddin ◽  
Muhammad Iqbal ◽  
Syed Ghulam Musharraf
Keyword(s):  
Double Bond ◽  
Critical Review ◽  
Structural Modification ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Side Chain ◽  
Synthetic Compounds ◽  
Efficient Approach ◽  
Cunninghamella Blakesleeana ◽  
Different Strains

: For several decades, biotransformational studies on steroidal compounds have gained a lot of attention because it is an efficient approach for the structural modification of complicated natural or synthetic compounds with high regio-, chemo- and stereoselectivity at environmentally friendly conditions. This review summarizes the use of different strains of Cunninghamella blakesleeana for the biotransformation of sixteen steroids 1-16 into a variety of transformed products. The transformed products may be important as a drug or precursor for the production of important pharmaceuticals. The types of reactions performed by C. blakesleeana include hydroxylation, epoxidation, reduction, demethylation, oxidation, glycosidation, double bond formation, side-chain degradation, isomerisation and opening of an isoxazol ring, which would be difficult to produce by traditional synthesis.

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