New Ozonide Chemistry
{'Code': '03090003', 'Directorate': {'Abbreviation': 'MPS', 'LongName': 'Direct For Mathematical & Physical Scien'}, 'Division': {'Abbreviation': 'CHE', 'LongName': 'Division Of Chemistry'}}
{'SignBlockName': 'Alfons Weber', 'PO_EMAI': None, 'PO_PHON': None}
This research will be supported by the Organic and                              Macromolecular Chemistry Program.  The work will lead to the                    development of new routes to heterocyclic compounds containing                  three oxygen atoms.  These are important constituent                            substructures in some important enviromental processes as well                  as having been discovered in a new antimalarial from mainland                   China, artemisin.                                                                                                                                               This will establish methods for the preparation of novel                        functional ozonides (1,2,4-trioxolanes) and to develop new                      reactions of these species which can be applied to compounds of                 chemical significance.  Although a great deal has been learned                  about the mechanism of alkene ozonolysis, very little is known                  of the chemistry of the product ozonides.  Likewise,                            substituent effects on the oxonide ring have not been                           well-studied.  The intramolecular carbonyloxide-ester                           cycloaddition will be further developed as a route to alkoxy                    oxonides, where the substituent exerts a strong electronic bias                 on the trioxolane system.  Two approaches will be                               explored--first, ozonolysis of alkene esters where a rigid                      carbon framework holds the reactive groups in close proximity,                  and the ozonation of cyclic vinyl ethers, where the reactive                    groups are generated together.  The alkoxy ozonides are                         selective oxygen transfer agents toward nucleophiles.  This                     process will be studied both on mechanistic grounds, including                  labelling experiments to determine the regioselectivity of                      0-transfer, and for synthetic utility--the oxidation of carbon                  nucleophiles is a problem of long standing.  The ozonation of                   allylic halides will be investigated to elucidate the                           stereoelectronic effects for ozonide formation.  The resulting                  beta-halo ozonides should be susceptible to ionization-ring                     expansion, thereby opening a new synthetic route to                             5-alkoxy-1,2,4-trioxanes, the pharmacophore of the antimalarial                 artemisinin.
{'FirstName': 'William', 'LastName': 'Bunnelle', 'PI_MID_INIT': 'H', 'PI_SUFX_NAME': None, 'PI_FULL_NAME': 'William H Bunnelle', 'EmailAddress': None, 'NSF_ID': '000298299', 'StartDate': '08/01/1988', 'EndDate': None, 'RoleCode': 'Principal Investigator'}
{'Name': 'University of Missouri-Columbia', 'CityName': 'COLUMBIA', 'ZipCode': '652113020', 'PhoneNumber': '5738827560', 'StreetAddress': '121 UNIVERSITY HALL', 'StreetAddress2': None, 'CountryName': 'United States', 'StateName': 'Missouri', 'StateCode': 'MO', 'CONGRESSDISTRICT': '04', 'CONGRESS_DISTRICT_ORG': 'MO04', 'ORG_UEI_NUM': 'SZPJL5ZRCLF4', 'ORG_LGL_BUS_NAME': 'UNIVERSITY OF MISSOURI SYSTEM', 'ORG_PRNT_UEI_NUM': None}
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{'Code': '1948', 'Text': 'SYNTHESIS'}
{'url': 'https://www.nsf.gov/awardsearch/download?DownloadFileName=1988&All=true', 'xml': '8806198.xml'}