Intramolecular electrophilic aromatic substitution of α-alkylcinnamaldehydes affording 1-alkoxy-2-alkylindenes

  • Jobashi T
  • Kawai A
  • Kawai S
 et al. 
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Abstract

Treatment of α-alkylcinnamaldehydes with orthoesters, alcohols, or thiols in the presence of BF3·OEt2induces an intramolecular electrophilic aromatic substitution reaction to afford 1-alkoxy-2-alkylindenes. The reaction mechanisms of the indene formation have been elucidated on the basis of the reaction behaviors of β-deuterated α-methylcinnamaldehyde and the NMR studies of the reaction mixture. The transformation process involves successive reactions, i.e., alkoxylation of the carbonyl carbon of α-alkylcinnamaldehydes to form acetals, elimination of alkoxide from the acetals to give alkoxycarbenium ion and γ-alkoxyallyl cation, and intramolecular electrophilic arylation to afford the indene ring structure. © 2006 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • 1-Alkoxy-2-alkylindene
  • Acetal
  • Alkoxylation
  • Intramolecular electrophilic arylation
  • α-Alkylcinnamaldehyde

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Authors

  • Takashi Jobashi

  • Atsushi Kawai

  • Satomi Kawai

  • Katsuya Maeyama

  • Hideaki Oike

  • Yasuhiko Yoshida

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