A Transient Vinylphosphinidene via a Phosphirene-Phosphinidene Rearrangement

Liu Leo Liu, Jiliang Zhou, Levy L. Cao, Ryan Andrews, Rosalyn L. Falconer, Christopher A. Russell, Douglas W. Stephan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A room-temperature-stable crystalline 2H-phosphirene (1) was prepared by treatment of an electrophilic diamidocarbene with tert-butylphosphaalkyne. Compound 1 is shown to react as a vinylphosphinidene generated via phosphirene-phosphinidene rearrangement. Thermolysis is shown to affect C-N bond scission while reactions with C6Cl4O2 or (tht)AuCl afford formal oxidation of the phosphindene center and the phosphinidene-insertion into an aromatic C-C bond of a mesityl group, respectively. The latter reaction is the first example of a phosphorus analog of the Büchner ring expansion reaction.

Original languageEnglish
Pages (from-to)147-150
Number of pages4
JournalJournal of the American Chemical Society
Issue number1
Early online date22 Dec 2017
Publication statusPublished - 10 Jan 2018


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