Phenyl Migration in Pseudohalogen Additions to 3,3,3-Triphenylpropene

Alfred Hassner, J. S. Teeter

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


Addition of iodine azide (IN3) to tritylethylene (1), unlike to i-butylethylene, leads to complete rearrangement producing 3-azido-2,3,3-triphenyl-1-propyl iodide (2) in 90% yield. Treatment of 2 with potassium t-butoxide gave triphenylacrolein. Under milder conditions it was possible to isolate an intermediate allylic azide. A rearranged product was also noted on iodine isocyanate addition to 1. Similarly, benzonorbornadiene gave a 1,3 adduct resulting from a Wagner-Meerwein phenyl migration and methylenenorbornene produced a rearranged IN3 adduct.

Original languageEnglish
Pages (from-to)3397-3401
Number of pages5
JournalJournal of Organic Chemistry
Issue number10
StatePublished - 1 Oct 1970
Externally publishedYes


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