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Synthesis of 2,5- and 2,6-bis(bromomethyl)-1,4-diphenylpiperazines and their conversion into 2,5-diphenyl-2,5-diazabicyclo[2.2.2]octane

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dc.contributor.author Nelson, David en_US
dc.contributor.author Worman, James en_US
dc.contributor.author Keen, Brian en_US
dc.date.accessioned 2006-07-19T19:54:02Z en_US
dc.date.available 2006-07-19T19:54:02Z en_US
dc.date.issued 1971-11-05 en_US
dc.identifier.citation The Journal of Organic Chemistry 36N22 (1971) 3361-3365 en_US
dc.identifier.issn 1520-6904 en_US
dc.identifier.uri http://hdl.handle.net/1850/2212 en_US
dc.description.abstract Treatment of cis-1,5-diphenyl-3,7-dihydroxyoctahydro-1,5-diazocine (1) with phosphorus tribromide yielded a mixture of cis-2,6-bis(bromomethyl)-1,4-diphenylpiperazine (4) and cis-2,5-bis(bromomethyl)-1,4-diphenylpiperazine ( 5 ). The structures of 4 and 5 were confirmed by conversion to the corresponding dimethyl-1,4- diphanylpiperazines (6 and 7) by lithium aluminum hydride. Compounds 6 and 7 were synthesized from cis-2,6- and cis-2,6-dimethylpiperazines. Both 4 and 5 on treatment with magnesium in tetrahydrofuran were converted to 2,5-diphenyl-2,5-diazabicyclo[2.2.2]octane (8). The interconversion of 4 and 5 is discussed. en_US
dc.description.sponsorship This research mas supported, in part, by Public Health Service Grant GM-13117. en_US
dc.format.extent 31371 bytes en_US
dc.format.mimetype application/pdf en_US
dc.language.iso en_US en_US
dc.publisher The American Chemical Society: The Journal of Organic Chemistry en_US
dc.title Synthesis of 2,5- and 2,6-bis(bromomethyl)-1,4-diphenylpiperazines and their conversion into 2,5-diphenyl-2,5-diazabicyclo[2.2.2]octane en_US
dc.type Abstract en_US
dc.subject.keyword Chemical synthesis en_US
dc.subject.keyword Interconversion en_US
dc.subject.keyword Stereochemistry en_US
dc.identifier.url http://dx.doi.org/10.1021/jo00821a020


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