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I.","year":"1975","journal-title":"Zh. Org. Khim."},{"key":"ref1\/cit1b","unstructured":"bKlimenko, V. I.; Sitkin, A. I.; Fridman, A. L.Vses. Nauchn. Konf. Khim. Tekhnol. Furanovykh Soedin. [Tezisy Dokl.],3rd, Riga, USSR1978,116."},{"key":"ref1\/cit1c","first-page":"1604","author":"Sitkin A. I.","year":"1977","journal-title":"Khim. Geterotsikl. Soedin."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"3579","DOI":"10.1039\/jr9610003579","author":"Kirby E. C.","year":"1961","journal-title":"J. Chem. Soc."},{"key":"ref3\/cit3","unstructured":"Goldmann, S.; Bechem, M.Ger. Offen.DE 4222770 A1, 1994. Neither details nor references regarding preparation, properties, and use of3l, are explicitly given."},{"key":"ref4\/cit4","unstructured":"Nitrogen tetroxide (or dinitrogen tetroxide, N2O4) is a powerful, highly toxic, and corrosive oxidizer:http:\/\/encyclopedia.airliquide.com\/sds\/en\/090_AL_EN.pdf."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1021\/cr60205a002","volume":"60","author":"Fanta P. E.","year":"1960","journal-title":"Chem. Rev."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"8382","DOI":"10.1021\/jo0488513","volume":"69","author":"Nishiwaki N.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1248\/yakushi1947.78.8_917","volume":"78","author":"Saikachi H.","year":"1958","journal-title":"Yakugaku Zasshi"},{"key":"ref7\/cit7a","unstructured":"aEian, G. L.; Trend, J. E.EP Patent 46083, 1982."},{"key":"ref7\/cit7b","unstructured":"bIn ref 7a, nitrocinnamylalcohol (2-nitro-3-phenylprop-2-en-1-ol,2m) was prepared from benzaldehyde and 2-nitroethanol; neither isomer configuration nor yields are given for2m."},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"811","DOI":"10.1021\/cr010043d","volume":"103","author":"Basavaiah D.","year":"2003","journal-title":"Chem. Rev."},{"key":"ref8\/ref8_2","unstructured":"(b)Ciganek, E."},{"key":"ref9\/cit9","unstructured":"Alonso Alonso, R.; Ozores Viturro, L.; Cagide Fagin, F.; Ortiz Lara, J. C.ES 2245603 A1; priority date June, 25th, 2004; WO 2006003227."},{"key":"ref10\/cit10a","doi-asserted-by":"crossref","first-page":"4745","DOI":"10.1016\/j.tetlet.2004.04.069","volume":"45","author":"Rastogi N.","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref10\/cit10b","doi-asserted-by":"crossref","first-page":"8073","DOI":"10.1016\/j.bmc.2006.07.035","volume":"14","author":"Mohan R.","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"ref11\/cit11","unstructured":"Pancratistatins comprise a family of antitumoral natural products; for the most recent reviews, see:"},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"341","DOI":"10.2174\/157017906777934872","volume":"3","author":"Chapleur Y.","year":"2006","journal-title":"Curr. Org. Synth."},{"key":"ref11\/cit11b","first-page":"365","author":"Rinner U.","year":"2005","journal-title":"Synlett"},{"key":"ref11\/cit11c","doi-asserted-by":"crossref","first-page":"1207","DOI":"10.1039\/b611967k","volume":"36","author":"Wilson R. M.","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"ref11\/cit11d","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1081\/BIO-200066621","volume":"33","author":"Pandey S.","year":"2005","journal-title":"Artif. Cells Blood Substit. Immobil. Biotechnol."},{"key":"ref11\/cit11e","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1007\/s10495-005-1896-x","volume":"10","author":"McLachlan A.","year":"2005","journal-title":"Apoptosis"},{"key":"ref11\/cit11f","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1007\/s00280-004-0941-8","volume":"56","author":"Kekre N.","year":"2005","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"4239","DOI":"10.1039\/B606277F","author":"Ortiz J. C.","year":"2006","journal-title":"Chem. Commun."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1023\/A:1019075227734","volume":"59","author":"Climent M. J.","year":"1999","journal-title":"Catal. Lett."},{"key":"ref14\/cit14","unstructured":"For details, see the Experimental Section and\/or theSupporting Information."},{"key":"ref15\/cit15a","doi-asserted-by":"crossref","first-page":"4155","DOI":"10.1021\/jo00170a070","volume":"48","author":"Dess D. B.","year":"1983","journal-title":"J. Org. Chem."},{"volume-title":"Basic Reactions in Organic Synthesis, Oxidation of Alcohols to Aldehydes and Ketones","year":"2006","author":"Tojo G.","key":"ref15\/cit15b"},{"issue":"29","key":"ref15\/cit15c","first-page":"3","volume":"68","author":"Plumb J. B.","year":"1990","journal-title":"Chem. Eng. News"},{"key":"ref17\/cit17a","unstructured":"aCrystallographic data for2a[EtOAc, C7H7NO4,M= 169.14, orthorhombic,a= 4.2404(10) \u00c5,b= 22.1197(6) \u00c5,c= 7.9235(2) \u00c5,V= 731.38 (3) \u00c53,T= 100 (2) K, space groupCc,Z= 4],2d[EtOAc, C7H7N1O3S1, M= 185.2, monoclinic,a= 11.4493(1) \u00c5,b= 5.0645(1) \u00c5,c= 13.6414(1) \u00c5,V= 760.419 (17) \u00c53,T= 100 (2) K, space groupP21\/n,Z= 4], and3d[C7H5N1O3S1,M= 183.2, monoclinic,a= 8.4333(3) \u00c5,b= 5.3908(2) \u00c5,c= 16.6554(6) \u00c5,V= 7736.10 (5) \u00c53,T= 100 (2) K, space groupP21\/n,Z= 4], have been deposited with the Cambridge Crystallographic Data Centre as CCDC 641192, 641193, and 641194, respectively, and can be obtained free of charge atwww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"ref17\/cit17b","first-page":"1201","volume":"9","author":"Panfilova L. V.","year":"1979","journal-title":"Khim. Geterotsikl. Soedin."},{"key":"ref18\/cit18","unstructured":"For crystallographic data of2d[CH2Cl2\u2212petroleum ether = 1\u20133,T= 293(2) K], see also ref 10b."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1107\/S0021889897003117","volume":"30","author":"Farrugia L. J.","year":"1997","journal-title":"J. Appl. Crystallogr."},{"key":"ref20\/cit20","unstructured":"See computational details in the Experimental Section."},{"key":"ref21\/cit21","unstructured":"Through this work, the C1\u2212C2 conformers of nitroenals3having the C1\u2550O and the C2\u2550C3 bondscis- andtrans-disposed are preferably termeds1,2-cis-enals and s1,2-trans-enals, respectively, even when the substituents of higher priority (the O atom of the carbonyl group at C1, and the nitro group at C2) are s1,2-trans-disposed in the first case and s1,2-cis-disposed in the second one."},{"key":"ref22\/cit22","unstructured":"Pretsch, E.; B\u00fchlmann, P.; Affolter, C.; Herrera, A.; Mart\u00ednez, R.Structure Determination of Organic Compounds;Springer:New York, 2002; p385."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"1942","DOI":"10.1023\/A:1014200612456","volume":"71","author":"Berestovitskaya V. M.","year":"2001","journal-title":"Russ. J. Gen. Chem."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1016\/j.jphotochem.2005.03.012","volume":"174","author":"Lasseuguette, E.","year":"2005","journal-title":"J. Photochem. Photobiol., A"},{"key":"ref25\/cit25","unstructured":"Preparation of3involves final oxidation with IBX. While caution should always be exercised when dealing with this reagent, we have routinely prepared and used it in batches of as much as 25 g without a single incident. See ref 15."},{"key":"ref26\/cit26","unstructured":"For spectra and\/or complete characterization data see theSupporting Information."},{"key":"ref27\/cit27","unstructured":"See also ref 10b."},{"key":"ref28\/cit28","unstructured":"At this stage, a simplified workup protocol, which simply involved addition ofn-hexane (6.5 mL), cooling to 0\u00b0 C, filtration, and solvent rotaevaporation at rt, was alternatively used in a number of cases."},{"key":"ref29\/cit29","unstructured":"See also ref 1."},{"key":"ref30\/cit30","unstructured":"Frisch, M. J.; et al.Gaussian 03, revision C.O1; Gaussian, Inc.: Wallingford, CT, 2004. See theSupporting Informationfor the full citation."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo702731b","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,5]],"date-time":"2023-03-05T18:52:56Z","timestamp":1678042376000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo702731b"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,4,23]]},"references-count":44,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2008,5,1]]}},"alternative-id":["10.1021\/jo702731b"],"URL":"https:\/\/doi.org\/10.1021\/jo702731b","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"type":"print","value":"0022-3263"},{"type":"electronic","value":"1520-6904"}],"subject":[],"published":{"date-parts":[[2008,4,23]]}}}