{"corpus_id":100541234,"paper_sha":"db93ca67882fa054c03afdf57d17e01a5ffbaf7e","doi":"10.3998/ARK.5550190.P008.436","arxiv_id":null,"pmid":null,"pmcid":null,"mag_id":2517198820,"dblp_id":null,"acl_id":null,"title":"Xenon difluoride in the organic laboratory: a tale of substrates, solvents and vessels","year":2013,"publication_date":"2013-12-17","venue":"","journal":{"name":"Arkivoc","pages":null,"volume":"2014"},"journal_issn":null,"journal_title":null,"publication_types":[],"pubmed_pub_types":null,"s2_fields_of_study":["Chemistry"],"reference_count":7,"citation_count":11,"influential_citation_count":0,"is_open_access":true,"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":"https://www.arkat-usa.org/get-file/49472/","s2_open_access_landing_url":"https://www.semanticscholar.org/paper/db93ca67882fa054c03afdf57d17e01a5ffbaf7e","s2_open_access_license":"CCBY","s2_open_access_status":"GOLD","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":"This Account summarises a series of studies of the reactions of xenon difluoride with organic substrates. It is concluded that xenon difluoride has two initial modes of reaction with organic substrates: single electron transfer (SET) and electrophilic addition. Reactions of aryltrimethylsilanes, carboxylic acids and esters, and trimethylsilyl enol ethers are discussed. The mode of reaction is determined by a combination of the solvent, the reaction vessel material and the presence of an acid catalyst. Pyrex, in the form of a flask surface, is a very effective catalyst for electrophilic reactions but this effect is inhibited by use of acetonitrile as solvent. Trimethylsilyl derivatives are particularly convenient substrates as these avoid the formation of HF, which may catalyse side-reactions. Some studies using [F]-XeF2 are described.","claims":[{"public_id":"cl_e750378ea628c855013f1772e8a7cab5","status":"active","text":"Pyrex flask surfaces strongly catalyze electrophilic reactions, and acetonitrile suppresses this catalytic effect.","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_e750378ea628c855013f1772e8a7cab5"},{"public_id":"cl_c623b8724add2599b483f7af16cac453","status":"active","text":"Studies using [F]-XeF2 are described.","confidence":0.82,"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_c623b8724add2599b483f7af16cac453"},{"public_id":"cl_82918dbe9fc2da6dc22e12095e43a2e0","status":"active","text":"The reaction pathway is determined by the solvent, the reaction 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