{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T18:35:15Z","timestamp":1787164515564,"version":"build-2736575974"},"reference-count":62,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2015,9,18]],"date-time":"2015-09-18T00:00:00Z","timestamp":1442534400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2015,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The methyltriphenylphosphonium methylcarbonate salt [Ph\n                    <jats:sub>3<\/jats:sub>\n                    PCH\n                    <jats:sub>3<\/jats:sub>\n                    ][CH\n                    <jats:sub>3<\/jats:sub>\n                    OCO\n                    <jats:sub>2<\/jats:sub>\n                    ], obtained directly by quaternarization of triphenylphosphine with dimethylcarbonate, is a latent ylide that promotes Wittig vinylation of aldehydes and ketones. Alkenes are obtained simply by mixing [Ph\n                    <jats:sub>3<\/jats:sub>\n                    PCH\n                    <jats:sub>3<\/jats:sub>\n                    ][CH\n                    <jats:sub>3<\/jats:sub>\n                    OCO\n                    <jats:sub>2<\/jats:sub>\n                    ] and the carbonyl and heating in a solvent (no base, no halides, and no inorganic byproducts). Deuterium exchange experiments and the particularly short anion\u2010cation distance measured by XRD in [Ph\n                    <jats:sub>3<\/jats:sub>\n                    PCH\n                    <jats:sub>3<\/jats:sub>\n                    ][CH\n                    <jats:sub>3<\/jats:sub>\n                    OCO\n                    <jats:sub>2<\/jats:sub>\n                    ] allowed to explain the nature and reactivity of this species. Green chemistry metrics (atom economy, mass index, environmental factor) indicate that this vinylation procedure is more efficient than comparable ones. Deuterated [Ph\n                    <jats:sub>3<\/jats:sub>\n                    PCD\n                    <jats:sub>3<\/jats:sub>\n                    ][CH\n                    <jats:sub>3<\/jats:sub>\n                    OCO\n                    <jats:sub>2<\/jats:sub>\n                    ] promoted the synthesis of deuterated olefins.\n                  <\/jats:p>","DOI":"10.1002\/cssc.201500935","type":"journal-article","created":{"date-parts":[[2015,9,18]],"date-time":"2015-09-18T07:06:52Z","timestamp":1442560012000},"page":"3963-3966","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Methyltriphenylphosphonium Methylcarbonate, an All\u2010In\u2010One Wittig Vinylation Reagent"],"prefix":"10.1002","volume":"8","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3217-422X","authenticated-orcid":false,"given":"Lisa","family":"Cattelan","sequence":"first","affiliation":[{"name":"Dipartimento di Scienze Molecolari e Nanosistemi Universit\u00e0 Ca' Foscari Venezia  Dorsoduro 2137 30123 Venezia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2969-6227","authenticated-orcid":false,"given":"Marco","family":"No\u00e8","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Molecolari e Nanosistemi Universit\u00e0 Ca' Foscari Venezia  Dorsoduro 2137 30123 Venezia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maurizio","family":"Selva","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Molecolari e Nanosistemi Universit\u00e0 Ca' Foscari Venezia  Dorsoduro 2137 30123 Venezia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicola","family":"Demitri","sequence":"additional","affiliation":[{"name":"Elettra\u2014Sincrotrone Trieste, S.S. 14 Km 163.5 in Area  Science Park 34149 Basovizza\u2014Trieste Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4544-8709","authenticated-orcid":false,"given":"Alvise","family":"Perosa","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Molecolari e Nanosistemi Universit\u00e0 Ca' Foscari Venezia  Dorsoduro 2137 30123 Venezia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,9,18]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00029a008"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19535800107"},{"key":"e_1_2_2_3_1","unstructured":"\u00a0"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja506497b"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60105f"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201208819"},{"key":"e_1_2_2_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201208819"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-32045-3_1"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja300943z"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000438"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000896"},{"key":"e_1_2_2_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000896"},{"key":"e_1_2_2_11_2","volume-title":"The Wittig reaction","author":"Maercker A.","year":"1965"},{"key":"e_1_2_2_12_1","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197704233"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19770890704"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197602981"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19760880908"},{"key":"e_1_2_2_15_2","unstructured":"H. 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