{"corpus_id":97520815,"paper_sha":"8a135fd7552d8734edc7517172fa97ea81845bd1","doi":"10.1055/S-1981-29317","arxiv_id":null,"pmid":null,"pmcid":null,"mag_id":2952834031,"dblp_id":null,"acl_id":null,"title":"The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products","year":1981,"publication_date":"1981-05-12","venue":"","journal":{"name":"Synthesis","pages":"1 - 28","volume":"1981"},"journal_issn":null,"journal_title":null,"publication_types":[],"pubmed_pub_types":null,"s2_fields_of_study":["Chemistry"],"reference_count":0,"citation_count":2746,"influential_citation_count":12,"is_open_access":false,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":null,"chemicals":null,"comments_corrections":null,"source_flags":1,"s2_open_access_pdf_url":null,"s2_open_access_landing_url":null,"s2_open_access_license":null,"s2_open_access_status":null,"pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"Abstract The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.","claims":[{"public_id":"cl_ebf34023a5f72ba38e990f94306d269f","status":"active","text":"Alcohols react with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters that convert into the corresponding carbonyl compounds.","confidence":0.95,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_ebf34023a5f72ba38e990f94306d269f"},{"public_id":"cl_815f067ff85f0ecbf61db864dca9006b","status":"active","text":"Diols are converted to cyclic ethers and hydroxy acids are converted to lactones using DEAD and TPP.","confidence":0.97,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_815f067ff85f0ecbf61db864dca9006b"},{"public_id":"cl_1a37d12a69b3d3c2fe08707165f505b0","status":"active","text":"Nucleosides react with DEAD and TPP to afford triphenylphosphoranylnucleosides.","confidence":0.96,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_1a37d12a69b3d3c2fe08707165f505b0"},{"public_id":"cl_8ccc5ea9127acb5082788f0aea242e56","status":"active","text":"The DEAD/TPP reagent system enables intermolecular dehydration between alcohols and acidic components including carboxylic acids, phosphoric diesters, imides, and active methylene compounds.","confidence":0.98,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_8ccc5ea9127acb5082788f0aea242e56"}],"concepts":[{"public_id":"co_0f4bfdde2534e759f367a6a79d51865f","status":"active","name":"diethyl azodicarboxylate","description":"An azo reagent used together with triphenylphosphine to promote dehydration and transformation reactions.","types":["reagent"],"aliases":["DEAD"],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_0f4bfdde2534e759f367a6a79d51865f"},{"public_id":"co_1a196a119f520433b122a5f92a4effce","status":"active","name":"cyclic ethers","description":"Ring-shaped ether products formed from diols in the described transformations.","types":["product class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_1a196a119f520433b122a5f92a4effce"},{"public_id":"co_3c854e79a3cf8906cdca618d482b462c","status":"active","name":"lactones","description":"Cyclic ester products formed from hydroxy acids.","types":["product class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_3c854e79a3cf8906cdca618d482b462c"},{"public_id":"co_3f07dae10e9fc89cba224e8b22998cfc","status":"active","name":"nucleosides","description":"Sugar-base conjugates that react here with the reagent system to form phosphoranylated products.","types":["compound class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_3f07dae10e9fc89cba224e8b22998cfc"},{"public_id":"co_724eac3f3c17ca601aef68f7279466fa","status":"active","name":"triphenylphosphine","description":"A phosphine reagent used with diethyl azodicarboxylate in synthetic transformations.","types":["reagent"],"aliases":["TPP"],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_724eac3f3c17ca601aef68f7279466fa"},{"public_id":"co_7518fb1b03e3a2b3ff764e9f776c6282","status":"active","name":"2,6-di-t-butyl-4-nitrophenol","description":"A hindered nitrophenol used as a reactant in the formation of aci-nitroester intermediates.","types":["compound"],"aliases":["BHTNO2"],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_7518fb1b03e3a2b3ff764e9f776c6282"},{"public_id":"co_8904524c27b79429f68ad47cf2ed56cb","status":"active","name":"triphenylphosphoranylnucleosides","description":"Nucleoside derivatives bearing a triphenylphosphoranyl group.","types":["product class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_8904524c27b79429f68ad47cf2ed56cb"},{"public_id":"co_892112eeff8e29b9b17bd5c1afd00584","status":"active","name":"imides","description":"Nitrogen-containing carbonyl compounds that can act as acidic components in the coupling reactions.","types":["compound class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_892112eeff8e29b9b17bd5c1afd00584"},{"public_id":"co_95f6e774c1c6d2d0731fee62e917e066","status":"active","name":"phosphoric diesters","description":"Phosphate ester compounds that can serve as acidic components in the reported reactions.","types":["compound class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_95f6e774c1c6d2d0731fee62e917e066"},{"public_id":"co_c14947b0efd7e3e2be8effff903220fd","status":"active","name":"carboxylic acids","description":"Organic acids containing a carboxyl group that participate as acidic coupling partners.","types":["compound class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_c14947b0efd7e3e2be8effff903220fd"},{"public_id":"co_d30f85165589c67460a30b3324dceec9","status":"active","name":"active methylene compounds","description":"Compounds with methylene groups activated by adjacent electron-withdrawing substituents.","types":["compound class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_d30f85165589c67460a30b3324dceec9"},{"public_id":"co_e524b7ae877f576219e8e16f16081d6a","status":"active","name":"intermolecular dehydration","description":"A condensation reaction in which water is removed between an alcohol and an acidic component.","types":["reaction"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_e524b7ae877f576219e8e16f16081d6a"},{"public_id":"co_eb14b0c0edb22ed02f9f633b4ba4e8c5","status":"active","name":"aci-nitroesters","description":"Nitro-containing ester intermediates formed from alcohols and 2,6-di-t-butyl-4-nitrophenol.","types":["intermediate"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_eb14b0c0edb22ed02f9f633b4ba4e8c5"},{"public_id":"co_fd873f562e3b67df7fc0b3f0cf7b3913","status":"active","name":"carbonyl compounds","description":"Compounds containing a carbonyl group, produced from aci-nitroester intermediates in the described sequence.","types":["product class"],"aliases":[],"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/concepts/co_fd873f562e3b67df7fc0b3f0cf7b3913"}],"external_ids":{"DOI":"10.1055/S-1981-29317","ArXiv":null,"PubMed":null,"PubMedCentral":null,"MAG":2952834031,"DBLP":null,"ACL":null},"open_access":{"is_open_access":false,"pdf_url":null,"landing_url":"https://sah.borca.ai/papers/97520815","source":null,"pdf_url_source":null,"license":null,"reason":"pdf_url_not_indexed"},"reference_availability":{"status":"unknown","references_indexed":false,"full_text_available":false,"full_text_source":null,"count_basis":"semantic_scholar_metadata","extraction_status":"not_applicable","reason":null},"source":{"provider":"episteme2","base_corpus":"semantic_scholar_dump","freshness_mode":"unknown","basis":["semantic_scholar_metadata","postgres_metadata"],"limits":["paper metadata is based on indexed upstream scholarly datasets","claims and concepts are available only for extracted papers","absence of claims or concepts means no extracted graph data is available in this response"],"status":"available","degraded":false,"degraded_reasons":[],"diagnostics":{"status":"available","degraded":false,"degraded_reasons":[],"metadata_status":"available","graph_status":"available","abstract_status":"available"},"source_flags":1},"paper_id":631024,"paper_uid":"34c7e99f-90b9-40ae-b329-3c2d94a31c68","canonical_identity":{"paper_id":631024,"paper_uid":"34c7e99f-90b9-40ae-b329-3c2d94a31c68","identity_status":"available","lookup_basis":"semantic_scholar_external_id","compatibility_path":"corpus_id"},"url":"https://sah.borca.ai/papers/97520815"}