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Search for "nitroalkane" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride
Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4
- towards the nitro group, which makes them highly susceptible to Michael addition [34]. While being stirred with the borohydride, the substrate progressively forms an α-carbanion in the newly formed nitroalkane, which ultimately leads to Michael addition to the nitrostyrene. Furthermore, studies to
Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3
Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83
- reaction was cooled to room temperature, and the product was isolated, either by adding 4 mL of water, which dissolves the DES, and extracting the nitroalkane with AcOEt, or by direct separation of the organic residue from the eutectic mixture (see below for recycling experiments and Supporting Information
- accomplished both in glycerol and in DES B, with the eutectic mixture generally performing better than glycerol alone; indeed, α-substituted nitroalkane 4h was isolated in 75% yield after 18 h of reaction at 60 °C. We further explored other DESs, and in particular, we turned our attention to betaine-containing
- with ammonia borane afforded product 6d in 61% isolated yield as 1:1 mixture of diastereomers (the diastereomeric ratio was not influenced by the reaction time, temperature or concentration). Finally, the possibility to develop a reliable, convenient protocol for the isolation of the nitroalkane and
Assessing the possibilities of designing a unified multistep continuous flow synthesis platform
Beilstein J. Org. Chem. 2018, 14, 1917–1936, doi:10.3762/bjoc.14.166
- kept in the feed storage tanks for preheating (see Figure 5). The reagents can be pumped with a suitable pump (viz., peristaltic pump, piston pump, diaphragm pump, etc.) into the mixer M5 and subsequently to reactor R5 which is packed with SiO2-NH2 and CaCl2. The intermediate nitroalkane obtained is
- where it is mixed with the nitroalkane stream. The reaction stream can then be passed through reactor R6 which is packed with polymer-supported (S)-pybox–calcium chloride and maintained at 0 °C. The reaction stream can be further passed to intermediate tank T6 where it can be preheated to 100 °C. The
Conjugate addition–enantioselective protonation reactions
Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116
- % yield, 95.5:4.5 to 97:3 er). The resulting nitroalkane adduct 159 could be reduced and cyclized to access α,γ-disubstituted γ-lactams. Ellman and co-workers, in the second example of conjugate addition–enantioselective protonation with nitroalkenes, showed that thioacids 160 could be added in high
Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems
Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248
- well as discuss current mechanistic understanding of these novel reactions. Keywords: alkene; alkylation; alkyne; catalysis; copper; nitroalkane; radical; Introduction Atom transfer radical (ATR) reactions are extremely useful in organic synthesis and polymer chemistry [1]. These reactions have been
- phenethylamine derivatives, many of which possess known biological activity. For instance, reduction of the fully substituted nitroalkane 19 provides phentermine (20), a clinically prescribed appetite suppressant (Scheme 4) [29][30]. While the precise mechanism of this transformation is not fully understood
- , internal alkenes (such as 39) were not affected during the reaction. Although the reaction proceeds via a distinct mechanism, the authors refer to the transformation as a formal Heck-type alkenylation of alkyl bromides. As with the nitroalkane alkylation chemistry illustrated above, this reaction is a rare
The chemistry of amine radical cations produced by visible light photoredox catalysis
Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234
- radical 134 concurrently. By carefully selecting reagents/conditions, either reactive intermediate can selectively participate in the designated reaction. As shown in Li and Wang’s work, iminium ion 133 is intercepted by nitroalkane to afford the aza-Henry product 135 while α-amino radical 134 is used to
C–C Bond formation catalyzed by natural gelatin and collagen proteins
Beilstein J. Org. Chem. 2013, 9, 1111–1118, doi:10.3762/bjoc.9.123
- ) reaction is a versatile and widely used base-catalyzed C–C bond forming reaction between a nitroalkane and an electrophilic carbonyl derivative (aldehyde or ketone) to produce β-nitroalcohols, which can be transformed into valuable synthetic building blocks [5][6][7][8][9][10]. Some biopolymers such as
- nitromethane (pKa = 10.2) the yield increased considerably (Table 3, entries 2, 6, 10 vs. 1, 5, 9, respectively), albeit without significant diastereoselectivity. Thus, acidity of the nitroalkane plays here a more important role than steric effects [28]. It is worth mentioning that control experiments in the
- organic media under mild conditions, affording the nitroaldol product in variable yields depending on the aldehyde and nitroalkane nature. Moreover, the scale-up of the process between 4-nitrobenzaldehyde and nitromethane could also be achieved on a 1 g scale and in good yield. A comparative kinetics
Continuous flow based catch and release protocol for the synthesis of α-ketoesters
Beilstein J. Org. Chem. 2009, 5, No. 23, doi:10.3762/bjoc.5.23
- . The overall process delivers synthetically useful α-ketoester products in high purity from various nitroalkane inputs and paves the way for more extended reaction sequences. The Uniqsis FlowSyn™ continuous flow reactor comprising of a column holder and heating unit (A) and the reactor coil (B). A
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