Tetrahedron

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

T Jobashi, A Kawai, S Kawai, K Maeyama, H Oike…

Index: Jobashi, Takashi; Kawai, Atsushi; Kawai, Satomi; Maeyama, Katsuya; Oike, Hideaki; Yoshida, Yasuhiko; Yonezawa, Noriyuki Tetrahedron, 2006 , vol. 62, # 24 p. 5717 - 5724

Full Text: HTML

Citation Number: 8

Abstract

Treatment of α-alkylcinnamaldehydes with orthoesters, alcohols, or thiols in the presence of BF3· OEt2 induces 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 ...