Intramolecular Cyclization of 1-(ω-Phenylalkyl)-2-(nitromethylene)pyrrolidines in Triflic Acid

Abstract

1-(ω-Phenylalkyl)-2-(nitromethylene)pyrrolidines in triflic acid undergo a C,O-diprotonation, followed by loss of water, to form conjugated iminium–hydroxynitrilium dications, which react with the tethered phenyl ring by electrophilic aromatic substitution to afford tricyclic iminium compounds as triflate salts. The scope and mechanism of this reaction are discussed.

GRAPHICAL ABSTRACT

Keywords:

• 1-(ω-Phenylalkyl)-2-(nitromethylene)pyrrolidines
• cation
• intramolecular cyclization
• triflate salts
• triflic acid

Notes

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