{"id":362,"date":"2018-05-18T14:27:59","date_gmt":"2018-05-18T14:27:59","guid":{"rendered":"https:\/\/sites.uni.edu\/chin\/?p=362"},"modified":"2018-05-18T16:15:09","modified_gmt":"2018-05-18T16:15:09","slug":"amazing-transformation","status":"publish","type":"post","link":"https:\/\/sites.uni.edu\/chin\/2018\/05\/18\/amazing-transformation\/","title":{"rendered":"Amazing transformation"},"content":{"rendered":"<p>This reaction always amazes me. It is the reaction of 6,6-dimethylfulvene with Ni(cod)2<\/p>\n<p><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00502a046\">Original McGlinchey prep where they used Ni atoms (coming in hot) to prepare the ligand.<\/a><\/p>\n<p><a href=\"https:\/\/doi.org\/10.1016\/j.ica.2008.04.025\">Our prep from 2009<\/a><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-363\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rxn.jpg\" alt=\"\" width=\"308\" height=\"66\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rxn.jpg 308w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rxn-300x64.jpg 300w\" sizes=\"auto, (max-width: 308px) 100vw, 308px\" \/><\/p>\n<p>Simple enough. The reaction uses the fulvene as both the solvent and reactant and yields a tar-like product. Really nasty looking stuff.<\/p>\n<figure id=\"attachment_364\" aria-describedby=\"caption-attachment-364\" style=\"width: 300px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-364 size-medium\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/crude-300x300.jpg\" alt=\"\" width=\"300\" height=\"300\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/crude-300x300.jpg 300w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/crude-150x150.jpg 150w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/crude-768x768.jpg 768w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/crude-1024x1024.jpg 1024w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><figcaption id=\"caption-attachment-364\" class=\"wp-caption-text\">Crude reaction mixture<\/figcaption><\/figure>\n<p>An extraction with hexane (a lot), filtration through a silica gel padded frit (a really big one), a nice orange solution is obtained. Rotovap to remove hexane.<\/p>\n<p>1970&#8217;s era Buchi rotovap doing work. <img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-372\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/keep-on-trucking2.jpg\" alt=\"\" width=\"177\" height=\"55\" \/><\/p>\n<div style=\"width: 854px;\" class=\"wp-video\"><video class=\"wp-video-shortcode\" id=\"video-362-1\" width=\"854\" height=\"480\" preload=\"metadata\" controls=\"controls\"><source type=\"video\/mp4\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rotovap-1.mp4?_=1\" \/><a href=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rotovap-1.mp4\">https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/rotovap-1.mp4<\/a><\/video><\/div>\n<p>Wash the resulting solid with chilled methanol and we get this.<\/p>\n<figure id=\"attachment_367\" aria-describedby=\"caption-attachment-367\" style=\"width: 300px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-367 size-medium\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/pure-300x300.jpg\" alt=\"\" width=\"300\" height=\"300\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/pure-300x300.jpg 300w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/pure-150x150.jpg 150w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/pure-768x768.jpg 768w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2018\/05\/pure-1024x1024.jpg 1024w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><figcaption id=\"caption-attachment-367\" class=\"wp-caption-text\">Pure ligand!<\/figcaption><\/figure>\n","protected":false},"excerpt":{"rendered":"<p>This reaction always amazes me. It is the reaction of 6,6-dimethylfulvene with Ni(cod)2 Original McGlinchey prep where they used Ni atoms (coming in hot) to prepare the ligand. Our prep from 2009 Simple enough. The reaction uses the fulvene as both the solvent and reactant and yields a tar-like product. Really nasty looking stuff. An [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"ocean_post_layout":"","ocean_both_sidebars_style":"","ocean_both_sidebars_content_width":0,"ocean_both_sidebars_sidebars_width":0,"ocean_sidebar":"0","ocean_second_sidebar":"0","ocean_disable_margins":"enable","ocean_add_body_class":"","ocean_shortcode_before_top_bar":"","ocean_shortcode_after_top_bar":"","ocean_shortcode_before_header":"","ocean_shortcode_after_header":"","ocean_has_shortcode":"","ocean_shortcode_after_title":"","ocean_shortcode_before_footer_widgets":"","ocean_shortcode_after_footer_widgets":"","ocean_shortcode_before_footer_bottom":"","ocean_shortcode_after_footer_bottom":"","ocean_display_top_bar":"default","ocean_display_header":"default","ocean_header_style":"","ocean_center_header_left_menu":"0","ocean_custom_header_template":"0","ocean_custom_logo":0,"ocean_custom_retina_logo":0,"ocean_custom_logo_max_width":0,"ocean_custom_logo_tablet_max_width":0,"ocean_custom_logo_mobile_max_width":0,"ocean_custom_logo_max_height":0,"ocean_custom_logo_tablet_max_height":0,"ocean_custom_logo_mobile_max_height":0,"ocean_header_custom_menu":"0","ocean_menu_typo_font_family":"","ocean_menu_typo_font_subset":"","ocean_menu_typo_font_size":0,"ocean_menu_typo_font_size_tablet":0,"ocean_menu_typo_font_size_mobile":0,"ocean_menu_typo_font_size_unit":"px","ocean_menu_typo_font_weight":"","ocean_menu_typo_font_weight_tablet":"","ocean_menu_typo_font_weight_mobile":"","ocean_menu_typo_transform":"","ocean_menu_typo_transform_tablet":"","ocean_menu_typo_transform_mobile":"","ocean_menu_typo_line_height":0,"ocean_menu_typo_line_height_tablet":0,"ocean_menu_typo_line_height_mobile":0,"ocean_menu_typo_line_height_unit":"","ocean_menu_typo_spacing":0,"ocean_menu_typo_spacing_tablet":0,"ocean_menu_typo_spacing_mobile":0,"ocean_menu_typo_spacing_unit":"","ocean_menu_link_color":"","ocean_menu_link_color_hover":"","ocean_menu_link_color_active":"","ocean_menu_link_background":"","ocean_menu_link_hover_background":"","ocean_menu_link_active_background":"","ocean_menu_social_links_bg":"","ocean_menu_social_hover_links_bg":"","ocean_menu_social_links_color":"","ocean_menu_social_hover_links_color":"","ocean_disable_title":"default","ocean_disable_heading":"default","ocean_post_title":"","ocean_post_subheading":"","ocean_post_title_style":"","ocean_post_title_background_color":"","ocean_post_title_background":0,"ocean_post_title_bg_image_position":"","ocean_post_title_bg_image_attachment":"","ocean_post_title_bg_image_repeat":"","ocean_post_title_bg_image_size":"","ocean_post_title_height":0,"ocean_post_title_bg_overlay":0.5,"ocean_post_title_bg_overlay_color":"","ocean_disable_breadcrumbs":"default","ocean_breadcrumbs_color":"","ocean_breadcrumbs_separator_color":"","ocean_breadcrumbs_links_color":"","ocean_breadcrumbs_links_hover_color":"","ocean_display_footer_widgets":"default","ocean_display_footer_bottom":"default","ocean_custom_footer_template":"","ocean_post_oembed":"","ocean_post_self_hosted_media":"","ocean_post_video_embed":"","ocean_link_format":"","ocean_link_format_target":"self","ocean_quote_format":"","ocean_quote_format_link":"post","ocean_gallery_link_images":"off","ocean_gallery_id":[],"footnotes":""},"categories":[1],"tags":[],"class_list":["post-362","post","type-post","status-publish","format-standard","hentry","category-uncategorized","entry"],"_links":{"self":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/362","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/comments?post=362"}],"version-history":[{"count":11,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/362\/revisions"}],"predecessor-version":[{"id":383,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/362\/revisions\/383"}],"wp:attachment":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/media?parent=362"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/categories?post=362"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/tags?post=362"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}