{"id":5950,"date":"2011-12-15T17:36:19","date_gmt":"2011-12-15T17:36:19","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=5950"},"modified":"2011-12-15T17:36:19","modified_gmt":"2011-12-15T17:36:19","slug":"molecular-gymnastics-in-22-cycloadditions-two-different-moves-compared","status":"publish","type":"post","link":"https:\/\/www.rzepa.net\/blog\/?p=5950","title":{"rendered":"Molecular gymnastics in  2+2 cycloadditions. Two different moves compared."},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"5950\">\n<p>The <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=5927\" target=\"_blank\">previous post<\/a> showed how the 2+2 cycloaddition of an alkene could occur by a sort of sideways insinuation of the bonds. I have also shown how the same reaction can occur with a dramatic rotation of one of the double bonds. This post compares the two moves side by side.<\/p>\n<p style=\"text-align: center;\"><a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/12\/a+s.svg\"><img decoding=\"async\" data-attachment-id=\"5952\" data-permalink=\"https:\/\/www.rzepa.net\/blog\/?attachment_id=5952\" data-orig-file=\"https:\/\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/a+s.svg\" data-orig-size=\"\" data-comments-opened=\"1\" data-image-meta=\"[]\" data-image-title=\"a+s\" data-image-description=\"\" data-image-caption=\"&lt;p&gt;Two different molecular dances.&lt;\/p&gt;\n\" data-medium-file=\"https:\/\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/a+s.svg\" data-large-file=\"https:\/\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/a+s.svg\" class=\"aligncenter  wp-image-5952\" title=\"a+s\" alt=\"\" src=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/12\/a+s.svg\" width=\"300\" \/><\/a><\/p>\n<table style=\"margin-left: auto; margin-right: auto;\" border=\"1\">\n<tbody>\n<tr>\n<td align=\"centre\"><a href=\"http:\/\/hdl.handle.net\/10042\/to-11413\" target=\"_blank\">0.0<\/a><\/td>\n<td align=\"centre\"><a href=\"http:\/\/hdl.handle.net\/10042\/to-11415\" target=\"_blank\">5.3 kcal\/mol<\/a><\/td>\n<\/tr>\n<tr>\n<td>\n<div id=\"attachment_5933\" style=\"width: 232px\" class=\"wp-caption aligncenter\"><a href=\"http:\/\/hdl.handle.net\/10042\/to-11331\"><img data-recalc-dims=\"1\" loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5933\" data-attachment-id=\"5933\" data-permalink=\"https:\/\/www.rzepa.net\/blog\/?attachment_id=5933\" data-orig-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?fit=464%2C283&amp;ssl=1\" data-orig-size=\"464,283\" data-comments-opened=\"1\" data-image-meta=\"{&quot;aperture&quot;:&quot;0&quot;,&quot;credit&quot;:&quot;&quot;,&quot;camera&quot;:&quot;&quot;,&quot;caption&quot;:&quot;&quot;,&quot;created_timestamp&quot;:&quot;0&quot;,&quot;copyright&quot;:&quot;&quot;,&quot;focal_length&quot;:&quot;0&quot;,&quot;iso&quot;:&quot;0&quot;,&quot;shutter_speed&quot;:&quot;0&quot;,&quot;title&quot;:&quot;&quot;}\" data-image-title=\"14d1\" data-image-description=\"\" data-image-caption=\"&lt;p&gt;Animation of a 2+2 thermal cycloaddition with no antarafacial components.&lt;\/p&gt;\n\" data-medium-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?fit=300%2C182&amp;ssl=1\" data-large-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?fit=450%2C274&amp;ssl=1\" class=\" wp-image-5933  \" title=\"14d1\" alt=\"\" src=\"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?resize=222%2C136\" width=\"222\" height=\"136\" srcset=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?w=464&amp;ssl=1 464w, https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/14d1.gif?resize=300%2C182&amp;ssl=1 300w\" sizes=\"auto, (max-width: 222px) 100vw, 222px\" \/><\/a><p id=\"caption-attachment-5933\" class=\"wp-caption-text\">The forbidden dance<\/p><\/div>\n<\/td>\n<td>\n<div id=\"attachment_5958\" style=\"width: 213px\" class=\"wp-caption aligncenter\"><a href=\"http:\/\/hdl.handle.net\/10042\/to-11399\"><img data-recalc-dims=\"1\" loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-5958\" data-attachment-id=\"5958\" data-permalink=\"https:\/\/www.rzepa.net\/blog\/?attachment_id=5958\" data-orig-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/2a%2B2s-CS1.gif?fit=254%2C179&amp;ssl=1\" data-orig-size=\"254,179\" data-comments-opened=\"1\" data-image-meta=\"{&quot;aperture&quot;:&quot;0&quot;,&quot;credit&quot;:&quot;&quot;,&quot;camera&quot;:&quot;&quot;,&quot;caption&quot;:&quot;&quot;,&quot;created_timestamp&quot;:&quot;0&quot;,&quot;copyright&quot;:&quot;&quot;,&quot;focal_length&quot;:&quot;0&quot;,&quot;iso&quot;:&quot;0&quot;,&quot;shutter_speed&quot;:&quot;0&quot;,&quot;title&quot;:&quot;&quot;}\" data-image-title=\"2a+2s-CS\" data-image-description=\"\" data-image-caption=\"&lt;p&gt;The allowed dance.&lt;\/p&gt;\n\" data-medium-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/2a%2B2s-CS1.gif?fit=254%2C179&amp;ssl=1\" data-large-file=\"https:\/\/i0.wp.com\/www.rzepa.net\/blog\/wp-content\/uploads\/2011\/12\/2a%2B2s-CS1.gif?fit=254%2C179&amp;ssl=1\" class=\" wp-image-5958 \" title=\"2a+2s-CS\" alt=\"\" src=\"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/12\/2a%2B2s-CS1.gif?resize=203%2C143\" width=\"203\" height=\"143\" \/><\/a><p id=\"caption-attachment-5958\" class=\"wp-caption-text\">The allowed dance.<\/p><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>As is sometimes the case in real life, the forbidden option has the lower activation barrier!<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 5950 -->","protected":false},"excerpt":{"rendered":"<p>The previous post showed how the 2+2 cycloaddition of an alkene could occur by a sort of sideways insinuation of the bonds. I have also shown how the same reaction can occur with a dramatic rotation of one of the double bonds. This post compares the two moves side by side. 0.0 5.3 kcal\/mol As [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[6],"tags":[1529,1527],"class_list":["post-5950","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-pericyclic","tag-tutorial-material"],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p1gPyz-1xY","jetpack_likes_enabled":true,"_links":{"self":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/5950","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=5950"}],"version-history":[{"count":0,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/5950\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=5950"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=5950"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=5950"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}