{"id":7633,"date":"2012-09-12T11:23:16","date_gmt":"2012-09-12T10:23:16","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=7633"},"modified":"2012-09-12T11:23:16","modified_gmt":"2012-09-12T10:23:16","slug":"the-history-of-stereochemical-notation-a-search-for-the-earliest-example","status":"publish","type":"post","link":"https:\/\/www.rzepa.net\/blog\/?p=7633","title":{"rendered":"The history of stereochemical notation: a search for the earliest example."},"content":{"rendered":"
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All organic chemists are familiar with the stereochemical notation for bonds, as shown below. But I had difficulty tracking down when it was introduced, and by whom. I offer a suggestion here, but if anyone reading this blog has got a better\/earlier attribution, please let us know!<\/p>\n

\"\"<\/p>\n

I suggest that the source is an article written by Derek Barton and R. C. Cookson in 1955 and published in 1956, entitled “The principles of conformational analysis” (DOI:\u00a0http:\/\/dx.doi.org\/10.1039\/QR9561000044<\/a>\u00a0). Some examples are shown below. Compound 19<\/strong> makes explicit the Fischer convention; 26\/27<\/strong> are indeed very modern, and 66<\/strong> uses not wedges but bold bonds (which is very common nowadays but suffers from having a slightly different semantic interpretation which was proposed by Maehr<\/a>).<\/p>\n

\"\"\"\"\"\"<\/p>\n

One might ask what another master of the period, R. B. Woodward was using. Thus in his 1956 article on the synthesis of lysergic acid<\/a>, we see this. Plenty of stereochemistry, but not annotated as per above! What you do find \u00a0(and with Barton as well) is essentially modern use of the arrow pushing conventions<\/a>, so by this period it was thoroughly established.\"\"<\/p>\n

Going back to 1951, we see Stork offering a stereospecific synthesis<\/a> (as far as I can tell, the first use of precisely this term in the literature). But in this example, there is no real need for clarification using the modern stereochemical notation.<\/p>\n

\"\"<\/p>\n

So, can anyone find examples of modern notation earlier than Barton’s usage?<\/p>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

All organic chemists are familiar with the stereochemical notation for bonds, as shown below. But I had difficulty tracking down when it was introduced, and by whom. I offer a suggestion here, but if anyone reading this blog has got a better\/earlier attribution, please let us know! I suggest that the source is an article […]<\/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":[1],"tags":[125,1528,909],"class_list":["post-7633","post","type-post","status-publish","format-standard","hentry","category-uncategorized","tag-derek-barton","tag-historical","tag-r-c-cookson"],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p1gPyz-1Z7","jetpack_likes_enabled":true,"_links":{"self":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/7633","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=7633"}],"version-history":[{"count":0,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/7633\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=7633"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=7633"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=7633"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}