The very first example of such reactivity was reported by Lambert, who demonstrated that nitromethane could react with benzene in the presence of AlCl3 to afford benzaldehyde oxime, which after acidic quench afforded aniline (7.11) (Scheme 7, Equation 3) (Lambert et al., 1949). Petteri Elsner, Hao Jiang, Johanne B. Nielsen, Filippo Pasi, Karl Anker Jørgensen. J. Formation of Nitriles, Carboxylic Acids, and Derivatives by Oxidation, Substitution, and Addition. Lee, J.-D. Wu, C.-W. Kuo, K.-S. Shia, Synlett, 2007, Finally, upon hydrolysis, primary amides 9.6 or the corresponding carboxylic acids were isolated (Scheme 9, Equation 1). selective catalyst for use in aerobic oxidations, hydrolytic oxidations and Xuanxuan Li, Shengyi Zhuang, Xinxin Fang, Ping Liu, Peipei Sun. Oxidative Intramolecular Cyclization of Diketoximes:  Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane1. W. Zhou, J. Xu, L. Zhang, N. Jiao, Org. nitriles from allylarenes or alkenes. chamber was filled with 8 ml of supporting electrolyte and introduced into the catholyte properly in order to minimize the space between the electrodes. One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes. Asymmetric Synthesis of a Chiral Building Block for Cyclopentanoids:  A Novel Enantioselective Synthesis of Preclavulone A. Shin-ya Tosaki,, Keiichi Hara,, Vijay Gnanadesikan,, Hiroyuki Morimoto,, Shinji Harada,, Mari Sugita,, Noriyuki Yamagiwa,, Shigeki Matsunaga, and. the corresponding alcohols, alkyl halides, or alkyl sulfonates without using The editor and reviewers' affiliations are the latest provided on their Loop research profiles and may not reflect their situation at the time of review. S. Chandrasekhar, K. Gopalaiah, Tetrahedron Lett., Miao Ding, Feng Zhou, Yun-Lin Liu, Cui-Hong Wang, Xiao-Li Zhao, Jian Zhou. Find more information about Crossref citation counts. The use of an O-protected oxime rather than an explosive O-protected Eur. A modular and organocatalytic approach to γ-butyrolactone autoregulators from Streptomycetes. Bull. ABDULKARIM H A MOHAMMED, GOPALPUR NAGENDRAPPA. 135, 2100-2103. Rafał Kowalczyk, Łukasz Sidorowicz, Jacek Skarżewski. Various ketoximes undergo the Beckmann rearrangement when heated with A metal-free C≡C bond cleavage of terminal alkynes in the presence of tBuONO Aliphatic nitro compounds. Electrophilic nitronate 9.2 initially formed in PPA, first underwent similar reaction with electron-rich arenes to afford phosphorylated species 9.3, and following elimination of phosphoric acid leading to formation of aldoxime 9.4. administration of primary nitroalkanes, other secondary nitroal-kanes, 2-methyl-2-nitropropane (a tertiary nitroalkane), and cyclopentan-one oxime. Scheme 2 Initial results to convert primary nitroalkanes to amides using UmAS. J. K. Augustine, R. N. Atta, B. K. Ramappa, C. Boodappa, Synlett, 2009, Although these compounds are typically employed after deprotonation at α-position as nucleophilic synthons, there is a possibility to exploit the umpolung method of activation. This practical method Kukushkin, David Tudela, Armando J.L. Low temperature quenching with methanol afforded cyclic oximes of isothiochromanones 11.9, and their higher cyclic homologs. benzylamines to the corresponding oximes in good yields is catalyzed by N,N′,N″-trihydroxyisocyanuric F.-E. Chen, Y.-Y. 24, 374–376. A number of new reactions of IBX with heteroatom-containing substrates were Scheme 3. benzylic or aliphatic primary azides. H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2013, 45, the Altmetric Attention Score and how the score is calculated. Aromatic aldoximes were dehydrated to the H. Zhao, C. P. Vandenbossche, S. G. Koenig, S. P. Singh, R. P. Bakale, Org. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). It should be pointed out that nitronates 1.12 could be generated in situ via addition of lithiumorganic compounds to trans-β-nitrostyrenes 1.11 and further reacted with Grignard reagents in the same manner (Scheme 1, Equation 4) (Fujisawa et al., 1983). Overall, instead of a new C-N bond formed in the reaction of higher primary nitroalkane homologs, here new C-C bond was introduced (Aksenov et al., 2012). Chim. Commun. doi: 10.1055/s-2008-1072767, Sartori, G., Bigi, F., Maggi, R., and Tomasini, F. (1994). Selective catalytic oxidative cleavage of oximes to carbonyl compounds with H2O2 over TS-1. Tetrahedron Lett. 2002, 1804-1806. The reaction of N-alkylhydroxylamines and aqueous filtration  and could be reused with minimal loss of activity. selectivity under mild conditions. 30, It was also demonstrated that nitronates 14.1 bearing β-CH bonds afford N-silyloxyenamines 14.2 upon sylilation. ecofriendly catalyst for the one-pot synthesis of nitriles from aldehydes under doi: 10.1002/hlca.19800630320, Cousson, A., and Coustard, J.-M. (1998). A straightforward and yields and high purities by a simple extraction of the reaction mixture with Iurre Olaizola, Teresa E. Campano, Igor Iriarte, Silvia Vera, Antonia Mielgo, Jesús M. García, José M. Odriozola, Mikel Oiarbide, Claudio Palomo. phosphoryltrichloride under mild conditions in very good yields. Dications stabilized by Y delocalization. It was also shown that derivatives of 1-(methylthio)-2-nitro-1-(phenylalkylthio)ethylene 11.6 in triflic acid provided nitrile oxide 11.7, which underwent facile intramolecular cyclization affording intermediate dications 11.8, which were detected by NMR spectroscopy. Mixed La–Li heterobimetallic complexes for tertiary nitroaldol resolution. Beckmann rearrangement of this oxime did not occur, probably, under highly acidic conditions it exists in diprotonated form. 6.17 Polonovski- and Pummerer-type Reactions and the Nef Reaction. efficiently converted into the corresponding nitriles in good yields by Chem. Aleksey Zaks,, Asha V. Yabannavar,, David R. Dodds,, C. Anderson Evans,, Pradip R. Das, and.