Facile Carbolithiation of Bent Alkyne without Catalyst. Tandem Route to Dibenzo[b,f]pentalenes from Dibenzocyclooctadiyne

Nucleophilic addition of RLi to a triple bond of dibenzocycloocta[a,e]diyne provides dibenzo[b,f]pentalene motif through trans-annulation of the resulting vinyllithium. Dibenzopentalene anion thus formed reacts with various electrophiles such as aldehydes, alkyl halides, acid halide, and Me3SiCl to...

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Bibliographic Details
Published inChemistry letters Vol. 37; no. 12; pp. 1296 - 1297
Main Authors Babu, Govindarajulu, Orita, Akihiro, Otera, Junzo
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.12.2008
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REARRANGEMENT
ACETYLENES
METALATION
ARYLMAGNESIATION
IRON
PYROLYSIS
ORGANOLITHIUM COMPOUNDS
CARBOMETALLATION
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Summary:Nucleophilic addition of RLi to a triple bond of dibenzocycloocta[a,e]diyne provides dibenzo[b,f]pentalene motif through trans-annulation of the resulting vinyllithium. Dibenzopentalene anion thus formed reacts with various electrophiles such as aldehydes, alkyl halides, acid halide, and Me3SiCl to give the corresponding products.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2008.1296