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Synthesis 1997; 1997(5): 524-526
DOI: 10.1055/s-1997-4505
short paper
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Unexpected Coupling Reaction of 9-Lithiobromomethylene-9H-fluorene with 6,6-Dicyclopropylfulvene

Gitendra C. Paul, Joseph J. Gajewski*
  • *Department of Chemistry, Indiana University, Bloomington, Indiana 47405, USA, Fax +1(812)8558300; E-mail: GAJEWSKI@INDIANA.EDU
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Publication Date:
31 December 2000 (online)

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Metallation of 9-bis(bromomethylene)-9H-fluorene with one equivalent of BuLi at -78°C followed by qhenching with 6,6-dicyclopropylfulvene and subsequent warming (room temperature, 18 h) gave an adduct identified as compound 5 (∼70% yield). Under identical conditions dimethylfulvene and cyclopropylmethylfulvene failed to give a similar adduct. Simple and efficient synthesis of 9-bromomethylene- and 9-bis(bromomethylene)-9H-fluorene are also described.

Reaction of 6 with dicyclopropylfulvene in the formation of 5

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