Nickel mediated double bond formation from vic-dibromides and ethyl magnesium bromide

1995 ◽  
Vol 36 (50) ◽  
pp. 9189-9192 ◽  
Author(s):  
Corrado Malanga ◽  
Laura A. Aronica ◽  
Luciano Lardicci
1970 ◽  
Vol 48 (23) ◽  
pp. 3742-3745 ◽  
Author(s):  
M. M. A. Hassan ◽  
A. F. Casy

The reaction between 3,3-diphenyl-3-cyano-1-methylpropyl isocyanate and ethyl magnesium bromide leads to 2-ethyl-5-methyl-3,3-diphenyl-1-pyrroline rather than the isomeric 2-ethylidenepyrrolidine. The protonated N-methyl analogue (identical with a major metabolite of methadone) retains the 1-pyrroline structure, but the free base is a cis-trans mixture of the corresponding 2-ethylidenepyrrolidines; the cis Me/Ph isomer preponderates and is the sole product (obtained as a quaternary salt) when the mixture is treated with methyl iodide. 5-Methyl-2-methylene-3,3-diphenylpyrrolidine, a lower homologue of the methadone metabolite, isomerizes to a 1-pyrroline derivative when protonated or methylated. All structural conclusions are based on i.r. and p.m.r. spectroscopic evidence.


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

2021 ◽  
Vol 18 ◽  
Author(s):  
Azizuddin ◽  
Muhammad Iqbal ◽  
Syed Ghulam Musharraf

: 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.


2015 ◽  
Vol 11 ◽  
pp. 1163-1174 ◽  
Author(s):  
Michael Weßling ◽  
Hans J Schäfer

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.


2010 ◽  
Vol 51 (14) ◽  
pp. 1822-1825 ◽  
Author(s):  
Thomas A. Ramirez ◽  
Baoguo Zhao ◽  
Yian Shi
Keyword(s):  

2018 ◽  
Vol 47 (25) ◽  
pp. 8402-8417 ◽  
Author(s):  
Lukas Keweloh ◽  
Niklas Aders ◽  
Alexander Hepp ◽  
Damian Pleschka ◽  
Ernst-Ulrich Würthwein ◽  
...  

A P–H functionalized FLP reacted with RX-CN by hydrophosphination. Ring opening by treatment with cyclopropenthione resulted in PC bond formation.


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