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Paper | Special issue | Vol 84, No. 2, 2012, pp.753-764
Published online, 15th August, 2011
DOI: 10.3987/COM-11-S(P)50
Molecular Recognition of 2-(Arylmethylthio)indolizine Derivatives through an Intramolecular Arene-π (Cation) Interaction

Akikazu Kakehi,* Kennosuke Itoh, Hiroyuki Suga, Nobuhiro Yamaguchi, Takashi Abe, Yohei Yuda, and Haruka Katsumata

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan

Abstract

Some 2-(arylmethylthio)indolizines bearing ethoxycarbonyl and/or cyano group(s) at the 1- and 3-positions were synthesized and their conformations were investigated by 1H-NMR spectra and X-ray analyses. Interestingly, it was indicated that the sulfide linkages in 2-(1-naphthylmethylthio)indolizine derivatives in CDCl3 solution are mainly present in gauche conformations and the intramolecular arene-π (cation) interactions reflect the electrophilic reactivity of the 1- and 3-substituents.