2562-37-0Relevant articles and documents
One-pot synthesis of nitroolefins using zeolite
Sreekumar,Padmakumar, Raghavakaimal,Rugmini
, p. 2695 - 2696 (1998)
Nitroolefins, versatile intermediates in organic synthesis, are conveniently prepared in yields by nitration of olefins using nitric oxide and zeolite as described.
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Griswold,A.A.,Starcher,P.S.
, p. 357 - 361 (1966)
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Reaction of Nitrogen Dioxide with Alkenes and Polyunsaturated Fatty Acids: Addition and Hydrogen Abstraction Mechanisms
Pryor, William A.,Lightsey, John W.,Church, Daniel F.
, p. 6685 - 6692 (1982)
The reactions of nitrogen dioxide in a carrier gas (nitrogen, oxygen, or air) with cyclohexene and a series of mono-, di-, and trienes is reported at NO2 concentrations ranging from 70 ppm to 50percent.A complete product analysis was made with cyclohexene, and these data allow the calculation of the fraction of the NO2 that reacts by addition to the double bond or by abstraction of an allylic hydrogen.At high concentrations of NO2, addition is the predominant process, in agreement with the literature.However, below 10 000 ppm (1percent), hydrogen abstraction predominates.We suggest this is because of competition between a reversible addition and an irreversible H-abstraction step, much as is the case for the well-known bromine atom reaction system.In fact, a kinetic analysis shows that the ratios of rate constants for addition and abstraction are similar for both NO2 and the bromine atom.A less direct method (analysis of water formed) was used to estimate the addition to abstraction ratio for other alkenes and for esters of unsaturated fatty acids; these data are in agreement with the cyclohexene data.The autoxidation of unsaturated fatty acid esters initiated by NO2 also was studied, and kinetic chain lengths and autoxidizability ratios are given.
A useful method for the conversion of olefins to nitro olefins
Reddy, G. Sudhakar,Corey
supporting information, p. 3399 - 3402 (2021/05/10)
Triflyl nitrate is easily generated from tetra-n-butylammonium nitrate in CH2Cl2 solution and serves as an effective nitrating agent for a wide range of unsaturated substrates to form nitro olefins.
tert-Butyl Nitrite Mediated Different Functionalizations of Internal Alkenes: Paths to Furoxans and Nitroalkenes
Mir, Bilal Ahmad,Singh, Sarangthem Joychandra,Kumar, Ritush,Patel, Bhisma K.
, p. 3801 - 3809 (2018/09/18)
tert-Butyl nitrite (TBN) reacts differently with various internal alkenes leading to interesting and useful products. Synthesis of 1,2,5-oxadiazole-N-oxides (furoxans) has been achieved from internal alkenes using tert-butyl nitrite (TBN), quinoline and K2S2O8. Under an identical reaction condition α,β-unsaturated carboxylic acids and cyclic and acyclic internal alkenes both afforded nitroalkenes as the sole product via decarboxylative and direct nitration path respectively. (Figure presented.).
A Deprotonation Approach to the Unprecedented Amino-Trimethylenemethane Chemistry: Regio-, Diastereo-, and Enantioselective Synthesis of Complex Amino Cycles
Trost, Barry M.,Wang, Youliang
supporting information, p. 11025 - 11029 (2018/07/30)
The first realization of the amino-trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino-trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo-, regio-, diastereo-, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino-trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.
