Regio- and Stereoselectivity in the Ene Reaction of N-Phenyl-l,2,4-triazoline-3,5-dione with, α,β-Unsaturated Carbonyl Substrates

Kyle J. Bottorff, Thomas R Hoye, Andrew J. Caruso, Joseph F. Dellarialb

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

N-Phenyltriazoline-3,5-dione reacts with, α,β-unsaturated ketones, esters, and lactones 1a-1 to give ene adducts 2a-1. The reactions usually proceed in good yield with high regioselectivity and, where possible, high stereoselectivity. Ene substrates capable of adopting an s-cis conformation show much greater reactivity. A variety of mechanistic interpretations is considered.

Original languageEnglish (US)
Pages (from-to)4287-4292
Number of pages6
JournalJournal of Organic Chemistry
Volume45
Issue number22
DOIs
StatePublished - Oct 1980

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