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Synlett 1999; 1999(5): 579-580
DOI: 10.1055/s-1999-2687
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Novel Synthesis of Exo-Benzocycloheptene-1,5-diones Utilizing Base-Mediated Tandem Carbocyclic Two-Atom Ring-Expansion Reaction of Hydroxy Methoxyallenylindanones

Ill-Yun Jeong* , Yoshimitsu Nagao
  • *Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan; Fax +81-8 86-33-95 03; E-mail: ynagao@ph2.tokushima-u.ac.jp
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Publication Date:
31 December 1999 (online)

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The intramolecular tandem two-carbon ring expansion was accomplished by the treatment of 2,2-dialkyl-3-hydroxy-3-(1-methoxyallenyl)indanones 1 with some strong bases to afford the corresponding exo-benzocycloheptene-1,5-diones 3.

hydroxy methoxyallenylindanone - amine base - allenyl ketone - ring-expansion - exo-benzocycloheptene-1,5-dione