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dc.contributor.authorCrawford, Sarah M.en_US
dc.contributor.authorThompson, Alisonen_US
dc.date.accessioned2013-08-12T17:55:02Z
dc.date.available2013-08-12T17:55:02Z
dc.date.issued2011en_US
dc.identifier.citationCrawford, Sarah M., and Alison Thompson. 2011. "Investigations into the nucleophilic meso-substitution of F-BODIPYs and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene." Heterocycles 83(2): 311-322.en_US
dc.identifier.issn0385-5414en_US
dc.identifier.urihttp://dx.doi.org/10.3987/COM-10-12099en_US
dc.identifier.urihttp://hdl.handle.net/10222/30700
dc.description.abstractA series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (totally unsubstituted dipyrrin skeleton), was optimized to give higher yields over routine literature procedures. This modified procedure involves oxidn. of a dipyrromethane using p-chloranil, instead of DDQ, to give a dipyrrin which is then trapped in situ as its BF2 complex. Nucleophilic meso-alkylation of the series of F-BOIDPYs with n-butyllithium gave meso-Bu F-BODIPYs in moderate to good yields. This work represents a new, synthetically viable method for the synthesis of meso-alkylated F-BODIPYs. Extension of the nucleophilic substitution methodol. to meso-arylation was possible. However, the reaction was unselective: substitution at boron, to give the boron-diaryl C-BOIDPYs, occurred preferentially to nucleophilic meso-substitution and thus a mixt. of products was obtained.en_US
dc.relation.ispartofHeterocyclesen_US
dc.titleInvestigations into the nucleophilic meso-substitution of F-BODIPYs and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene.en_US
dc.title.alternativeSection Title: Organometallic and Organometalloidal Compoundsen_US
dc.typearticleen_US
dc.identifier.volume83en_US
dc.identifier.issue2en_US
dc.identifier.startpage311en_US
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