dc.contributor.author | Crawford, Sarah M. | en_US |
dc.contributor.author | Thompson, Alison | en_US |
dc.date.accessioned | 2013-08-12T17:55:02Z | |
dc.date.available | 2013-08-12T17:55:02Z | |
dc.date.issued | 2011 | en_US |
dc.identifier.citation | Crawford, 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.issn | 0385-5414 | en_US |
dc.identifier.uri | http://dx.doi.org/10.3987/COM-10-12099 | en_US |
dc.identifier.uri | http://hdl.handle.net/10222/30700 | |
dc.description.abstract | A 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.ispartof | Heterocycles | en_US |
dc.title | 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. | en_US |
dc.title.alternative | Section Title: Organometallic and Organometalloidal Compounds | en_US |
dc.type | article | en_US |
dc.identifier.volume | 83 | en_US |
dc.identifier.issue | 2 | en_US |
dc.identifier.startpage | 311 | en_US |