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The reactivity pattern of representative 1\u2010ethyl\u20103\u2010methyl\u2010NHO\u2013CO<jats:sub>2<\/jats:sub> adduct <jats:bold>4<\/jats:bold> has been investigated and compared with the corresponding NHC\u2013CO<jats:sub>2<\/jats:sub> zwitterion: The protonation of <jats:bold>4<\/jats:bold> with HX led to the imidazolium salts [NHO\u2013CO<jats:sub>2<\/jats:sub>H][X], which underwent decarboxylation to [EMMIm][X] in the presence of nucleophilic catalysts. NHO\u2013CO<jats:sub>2<\/jats:sub> zwitterion <jats:bold>4<\/jats:bold> can act as an efficient carboxylating agent towards CH acids such as acetonitrile. The [EMMIm] cyanoacetate and [EMMIm]<jats:sub>2<\/jats:sub> cyanomalonate salts formed exemplify the first C\u2212C bond\u2010forming carboxylation reactions with NHO\u2010activated CO<jats:sub>2<\/jats:sub>. The reaction of the free NHO with dimethyl carbonate selectively led to methoxycarbonylated NHO, which is a perfect precursor for the synthesis of functionalized ILs [NHO\u2013CO<jats:sub>2<\/jats:sub>Me][X]. The first NHO\u2010SO<jats:sub>2<\/jats:sub> adduct was synthesized and structurally characterized; it showed a similar reactivity pattern, which allowed the synthesis of imidazolium methyl sulfites upon reaction with methanol.<\/jats:p>","DOI":"10.1002\/chem.201602973","type":"journal-article","created":{"date-parts":[[2016,9,22]],"date-time":"2016-09-22T08:26:47Z","timestamp":1474532807000},"page":"16292-16303","source":"Crossref","is-referenced-by-count":35,"title":["N\u2010Heterocyclic Olefin\u2013Carbon Dioxide and \u2013Sulfur Dioxide Adducts: Structures and Interesting Reactivity Patterns"],"prefix":"10.1002","volume":"22","author":[{"given":"Lars H.","family":"Finger","sequence":"first","affiliation":[{"name":"Fachbereich Chemie and Materials Science Centre Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 4 35043 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jannick","family":"Guschlbauer","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie and Materials Science Centre Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 4 35043 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Klaus","family":"Harms","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie and Materials Science Centre Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 4 35043 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f6rg","family":"Sundermeyer","sequence":"additional","affiliation":[{"name":"Fachbereich Chemie and Materials Science Centre Philipps-Universit\u00e4t Marburg  Hans-Meerwein-Strasse 4 35043 Marburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,9,22]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","unstructured":"R.Kalb(PROIONIC) WO 2008052861 2008;"},{"key":"e_1_2_6_3_2","unstructured":"R.Kalb(PROIONIC) WO 2008052860 2008;"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700055"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/B918713H"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b920003g"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/bk-2003-0856.ch008"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00698j"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.201300150"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC06224A"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.5b01665"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504577"},{"key":"e_1_2_6_13_1","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056625k"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0742885"},{"key":"e_1_2_6_16_2","first-page":"88","volume":"35","author":"Voutchkova A. 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