Intramolecular Photoaddition of Secondary α-(Aminoalkyl)styrenes

Frederick D. Lewis*, Dario M. Bassani, G. Dasharatha Reddy

*Corresponding author for this work

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

The photophysical and photochemical behavior of a series of α-[(N-methylamino)alkyl]styrenes with two to four methylenes separating the styryl and amino groups and an (aminoalkyl) indene have been investigated and the results compared to those for the intermolecular reaction of α-methylstyrene with diethylamine. Both inter- and intramolecular quenching of styrene fluorescence by the amine is observed, indicative of electron-transfer quenching as the initial step in these reactions. The resulting exciplex undergoes regioselective N-H proton transfer to styrene C-β yielding a biradical, in the case of the intramolecular reaction, and a radical pair, in the case of the intermolecular reaction. Biradical or radical pair combination yields styrene-amine addition products. The conformation of the intermediate exciplex is proposed to control the regioselectivity of the intramolecular N-H proton transfer process.

Original languageEnglish (US)
Pages (from-to)6390-6393
Number of pages4
JournalJournal of Organic Chemistry
Volume58
Issue number23
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Organic Chemistry

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