{"id":9728,"date":"2014-01-09T10:51:05","date_gmt":"2014-01-09T09:51:05","guid":{"rendered":"https:\/\/web.computaex.es\/?page_id=9728"},"modified":"2025-08-27T10:54:57","modified_gmt":"2025-08-27T08:54:57","slug":"effect-of-configuration-of-2-vinyldiazocarbonyl-compounds-on-their-reactivity-experimental-and-computational-study","status":"publish","type":"page","link":"https:\/\/computaex.es\/en\/publicaciones\/effect-of-configuration-of-2-vinyldiazocarbonyl-compounds-on-their-reactivity-experimental-and-computational-study\/","title":{"rendered":"Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study"},"content":{"rendered":"<div class=\"field field-name-field-pub-descripcion field-type-text-long field-label-hidden\">\n<div class=\"field-items\">\n<div class=\"field-item even\">\n<p>Supurgibekov, Murat B. and Cantillo, David and Kappe, C. Oliver and Surya Prakash, G. K. and Nikolaev, Valerij A.\u00a0<strong>Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study<\/strong>. Org. Biomol. Chem. Volume 12, January 2014, Pages 682-689.\u00a0<a href=\"http:\/\/dx.doi.org\/10.1039\/C3OB42102C\" target=\"_blank\" rel=\"noopener\">http:\/\/dx.doi.org\/10.1039\/C3OB42102C.<\/a><\/p>\n<p><strong>Abstract<\/strong><br \/>\nNon-fluorinated vinyldiazo compounds with <em>trans<\/em>-configuration irrespective of the nature of 3-R<small><sup>1<\/sup><\/small>-substituent (R<small><sup>1<\/sup><\/small>\u00a0= H, Me, TBSO) even under ambient conditions easily cyclize to produce pyrazoles, while\u00a0<em>cis<\/em>-stereoisomers undergo similar ring closure only at elevated temperatures or decompose to produce vinyloxocarbene reaction products. The 3-CF<small><sub>3<\/sub><\/small>-substituted analogues with\u00a0<em>cis<\/em>&#8211; or\u00a0<em>trans<\/em>-configuration do not produce pyrazoles at all, but on heating furnish only vinylcarbene derived products. DFT calculations of theoretical energy barriers adequately explain the different experimental reactivity found for stereoisomeric vinyldiazocarbonyl compounds, and a new model for their interconversion through the corresponding pyrazoles has been suggested.<\/p>\n<div class=\"capsule__column-wrapper\">\n<div class=\"capsule__article-image fixpadv--s\"><img decoding=\"async\" src=\"https:\/\/pubs.rsc.org\/en\/Image\/Get?imageInfo.ImageType=GA&amp;imageInfo.ImageIdentifier.ManuscriptID=C3OB42102C&amp;imageInfo.ImageIdentifier.Year=2014\" alt=\"Graphical abstract: Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study\" \/><\/div>\n<div><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"field field-name-field-pub-fuente field-type-text-long field-label-above\">\n<div class=\"field-label\">Fuente de la publicaci\u00f3n:<\/div>\n<div class=\"field-items\">\n<div class=\"field-item even\">\n<ul>\n<li><a href=\"http:\/\/pubs.rsc.org\/en\/Content\/ArticleLanding\/2014\/OB\/c3ob42102c#!divAbstract\" target=\"_blank\" rel=\"noopener\">Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>","protected":false},"excerpt":{"rendered":"<p>Supurgibekov, Murat B. and Cantillo, David and Kappe, C. Oliver and Surya Prakash, G. K. and Nikolaev, Valerij A.\u00a0Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational &#8230;<\/p>","protected":false},"author":1,"featured_media":0,"parent":1583,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"categories":[110,91],"tags":[],"class_list":["post-9728","page","type-page","status-publish","hentry","category-anteriores","category-publicaciones"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.1.1 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study - Fundaci\u00f3n COMPUTAEX<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/computaex.es\/en\/publicaciones\/effect-of-configuration-of-2-vinyldiazocarbonyl-compounds-on-their-reactivity-experimental-and-computational-study\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study - Fundaci\u00f3n COMPUTAEX\" \/>\n<meta property=\"og:description\" content=\"Supurgibekov, Murat B. and Cantillo, David and Kappe, C. 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