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B.","year":"1993","journal-title":"Chem. Eng. News"},{"key":"ref11\/cit11c","doi-asserted-by":"publisher","DOI":"10.1021\/op990045o"},{"key":"ref12\/cit12a","unstructured":"aIsolated yields\nafter column chromatography."},{"key":"ref12\/cit12b","unstructured":"bThe ratio of alkene isomers was determined by GC-MS analyses\nof the crude reaction mixtures with an assumption that they elicited\nan identical response."},{"key":"ref12\/cit12c","unstructured":"cThe alkene geometry of the major isomer was deduced by NOE."},{"key":"ref12\/cit12d","unstructured":"dThe calculated ratio of alkene\nisomers may not be reflective of the actual ratio in the crude reaction\nmixtures due the possibility for some alkenes to isomerize under our\nGC conditions, e.g. compounds\n                      13c\n                      and\n                      14c\n                      ."},{"key":"ref12\/cit12e","unstructured":"eThe lower\nisolated product yields in some examples were due to the high volatility\nof the alkenes."},{"key":"ref12\/cit12f","unstructured":"fThe content of an alkyl chloride in the crude reaction\nmixture, as determined by GC-MS with an assumption that they elicited\nan identical response, typically ranges between 0% to 9%. The only\nexception is substrate\n                      8d\n                      , which produced 18% of the\nchlorination product. See Table S-1 and\nGC chromatograms in the Supporting Information for details on each substrate."},{"key":"ref13\/cit13a","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01567D"},{"key":"ref14\/cit14a","doi-asserted-by":"publisher","DOI":"10.1021\/jo00261a039"},{"key":"ref15\/cit15a","doi-asserted-by":"publisher","DOI":"10.1021\/ja01512a034"},{"key":"ref15\/cit15b","doi-asserted-by":"publisher","DOI":"10.1021\/jo01088a620"},{"key":"ref15\/cit15c","doi-asserted-by":"publisher","DOI":"10.1021\/cr60207a001"},{"key":"ref17\/cit17a","unstructured":"aDehydration\nof substrate\n                      4\n                      with catalytic TsOH (0.1 equiv) in dichloromethane\n(0.5 M) at reflux furnished alkenes\n                      5\n                      and\n                      6\n                      as a 62:38 mixture. Had our reaction proceeded primarily via the\nE1 mechanism, we believed that poorer (\n                      E\n                      ) vs (\n                      Z\n                      ) alkene selectivity as well as the Zaitzev preference\nwould have been observed."},{"key":"ref17\/cit17b","unstructured":"bFor comparison, dehydration of substrate\n                      4\n                      was performed with SOCl\n                      2\n                      or POCl\n                      3\n                      in\nthe presence of pyridine, see refs (3) and (4), respectively. Treatment with SOCl\n                      2\n                      (1.5 equiv)\nand pyridine (5.0 equiv) produced a 41:8:51 mixture of products\n                      5\n                      :\n                      6\n                      :\n                      7\n                      , whereas POCl\n                      3\n                      (2.5\nequiv) and pyridine (15 equiv) furnished alkene mixtures\n                      5\n                      :\n                      6\n                      in a 81:19 ratio without the presence of alkyl chloride\n                      7\n                      ."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.9b01959","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,27]],"date-time":"2023-04-27T12:16:05Z","timestamp":1682597765000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.orglett.9b01959"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,6,28]]},"references-count":44,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2019,7,19]]}},"alternative-id":["10.1021\/acs.orglett.9b01959"],"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.9b01959","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,6,28]]}}}