Tröger's base is a Λ-shaped molecule containing a 1,5-diazabicyclo[3.3.1]nona-2,6-diene subunit that is formed from the reaction between an aniline and formaldehyde. During the synthesis of derivatives of this ring system formed from fluorescent 4-amino-N-3-bromopropyl-1,8-naphthalimide, we observed an unexpected concomitant hydrolysis of the bromide to give the 3-hydroxypropyl compound. We have subsequently observed that the reactions of 4-alkylamino-N-allyl-1,8-naphthalimides involve anchimeric assistance by the carbonyl oxygen of the fluorophore. The scope and limitations of this anchimeric assistance will be discussed.

Anchimeric assistance in reactions of N-allyl-4-alkylamino-1,8-naphthalimides

255th National Meeting (2018)

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