The\u00a0Pinnick oxidation<\/strong>\u00a0is also known as\u00a0Lindgren oxidation. It is an\u00a0organic reaction\u00a0by which\u00a0aldehydes\u00a0can be oxidized into its corresponding\u00a0carboxylic acid, originally developed by Lindgren and Nilsson.^{ref1 \u00a0\u00a0\u00a0\u00a0<\/sup>\u00a0The typical reaction condition used today was modified by G. A. Kraus even before Pinnick.ref2,3\u00a0 Pinnick proved this condition as general. There are number of ways to oxidize the aldehydes however, only few reactions are endurable to the broad range of\u00a0functional groups. One of such reaction is Pinnick Oxidation which can provide preferred transformation even to systems that contain sensitive functionalities or\u00a0sterically hindered\u00a0groups. This reaction is especially useful for oxidizing \u03b1-methylene aldehyde units.ref4 It is an inexpensive method for effectively oxidizing aldehydes instereospecific\u00a0manner. The reaction is named after\u00a0chemist\u00a0H.W. Pinnick.<\/p>\n}

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\n Mechanism<\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n Following\u00a0reaction mechanism\u00a0was proposed for Pinnick Oxidation. However, the mechanism follows formation of a\u00a0by-product\u00a0that can cause a side reaction which can inevitably consume NaClO2<\/sub>. Therefore, the reaction requires the use of\u00a0scavengers\u00a0to be able to remove the by-products.6<\/h2>\n \n <\/a><\/div>\n \u00a0<\/div>\n \u00a0<\/div>\n \u00a0<\/div>\n <\/div>\n \u00a0<\/div>\n \u00a0<\/div>\n \n Synthetic Uses<\/h2>\n Zaragozic acid<\/a>\u00a0is a potent\u00a0squalene synthase\u00a0inhibitor\u00a0that can reduce the side effects caused by\u00a0cholesterol\u00a0inhibiting drugs which can also interfere with the production of important\u00a0steroids. The total synthesis of Zaragozic acid applied by A. Armstrong was possible through Pinnick Oxidation. Different oxidation methods such as\u00a0Jones oxidation, modified\u00a0Ley Oxidation were also applied. However, the efforts resulted in a mixture of products. A good yield with good purity could be obtained via Pinnick Oxidation.<\/p>\n \n <\/a><\/div>\n<\/div>\n<\/div>\n \u00a0<\/div>\n<\/div>\n \u00a0<\/h2>\n References<\/h2>\n \n Lindgren, Bengt O.; Nilsson, Torsten; Husebye, Steinar; Mikalsen, \u00d8Yvind; Leander, Kurt; Swahn, Carl-Gunnar (1973). “Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite”.\u00a0Acta Chemica Scandinavica<\/em>\u00a027<\/strong>: 888.\u00a0doi<\/a>:10.3891\/acta.chem.scand.27-0888<\/a>.<\/li>\n George A. Kraus; Bruce Roth (1980). “Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system”.\u00a0The Journal of Organic Chemistry<\/em>\u00a045<\/strong>: 4825.\u00a0doi<\/a>:10.1021\/jo01312a004<\/a>.<\/li>\n George A. Kraus; Michael J. Taschner (1980). “Model studies for the synthesis of quassinoids. 1. Construction of the BCE ring system”.The Journal of Organic Chemistry<\/em>\u00a045<\/strong>: 1175.\u00a0doi<\/a>:10.1021\/jo01294a058<\/a>.<\/li>\n Bal, B. S.; Childers, W.E.; Pinnick, H.W. (1981). “Oxidation of \u03b1,\u03b2-Unsaturated Aldehydes”.\u00a0Tetrahedron<\/a><\/em>\u00a037<\/strong>: 2091\u20132096.doi<\/a>:10.1016\/S0040-4020(01)97963-3<\/a>.<\/li>\n Mundy, B.J; Michael G. Ellerd, Frank G. Favaloro (2005).\u00a0Name reactions and reagents in organic synthesis<\/em>. John Wiley & Sons.\u00a0ISBN<\/a>\u00a00-471-22854<\/a>.<\/li>\n<\/ol>\n \u00a06\u00a0 Corey, E.J; K.C. Nicolaou (2005).\u00a0Strategic Applications of Named Reactions<\/em>. Elsevier, Inc.\u00a0ISBN<\/a>\u00a0978-7-03-019190-8<\/a>.<\/p>\n <\/p>\n <\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":" The\u00a0Pinnick oxidation\u00a0is also known as\u00a0Lindgren oxidation. It is an\u00a0organic reaction\u00a0by which\u00a0aldehydes\u00a0can be oxidized into its corresponding\u00a0carboxylic acid, originally developed by Lindgren and Nilsson.ref1 \u00a0\u00a0\u00a0\u00a0\u00a0The typical reaction condition used today was modified by G. A. Kraus even before Pinnick.ref2,3\u00a0 Pinnick proved this condition as general. There are number of ways to oxidize the aldehydes however, only… Continue reading Pinnick oxidation<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[144],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/323"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=323"}],"version-history":[{"count":13,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/323\/revisions"}],"predecessor-version":[{"id":443,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/323\/revisions\/443"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=323"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=323"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=323"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}