195520-09-3Relevant academic research and scientific papers
Preparation method of nitroolefin derivative with nitrate as nitro source
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Paragraph 0042; 0112-0117; 0133-0135, (2019/08/20)
The invention relates to a nitroolefin derivative with nitrate as nitro source and a preparation method thereof. Under the atmosphere of nitrogen, an olefin compound, nitrate, trimethylchlorosilane (TMSC1) and copper salt are stirred in acetonitrile at 0-30 DEG C; in addition, the reaction degree is monitored by using a TLC point plate; after the olefin compound is completely consumed, alkali is added to an obtained mixture to be stirred for 20-30 min; then after a solvent is removed from an obtained mixture by using a rotary evaporator, the nitroolefin derivative can be obtained through silicagel column purification. Compared with the prior art, the nitroolefin derivative with the nitrate as the nitro source, provided by the invention, has the advantages of mild reaction condition, high yield, high E type selectivity and the like.
Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO
Manna, Srimanta,Jana, Sandipan,Saboo, Tapish,Maji, Arun,Maiti, Debabrata
supporting information, p. 5286 - 5288 (2013/06/27)
Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction. The Royal Society of Chemistry 2013.
Stereoselective nitration of olefins with tBuONO and TEMPO: Direct access to nitroolefins under metal-free conditions
Maity, Soham,Naveen, Togati,Sharma, Upendra,Maiti, Debabrata
supporting information, p. 3384 - 3387 (2013/07/26)
Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.
A predictably selective nitration of olefin with Fe(NO3) 3 and TEMPO
Naveen, Togati,Maity, Soham,Sharma, Upendra,Maiti, Debabrata
, p. 5949 - 5954 (2013/07/26)
Ferric nitrate with catalytic TEMPO has been identified as a useful reagent for regio- and stereoselective nitration of a wide variety of aromatic, aliphatic, and heteroaromatic olefins. This reaction provided nitroolefins in preparatively useful yields with excellent E-selectivity. Due to its mild nature and operational simplicity, the present protocol is expected to find application in synthetic setup.
Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO
Maity, Soham,Manna, Srimanta,Rana, Sujoy,Naveen, Togati,Mallick, Arijit,Maiti, Debabrata
supporting information, p. 3355 - 3358 (2013/04/10)
Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.
