Fragmentation of 2,2,2-triphenylethoxychlorocarbene: Evidence for ultrafast fragmentation-rearrangement in excited diazirines

Xiaolin Fu, Robert A. Moss, Piotr Piotrowiak, Mykhaylo Myahkostupov, Ian Gould

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

(Chemical Equation Presented) Photolysis of 3-(2,2,2-triphenylethoxy)-3- chlorodiazirine gives 2,2,2-triphenylethoxychlorocarbene which fragments with 1,2-phenyl migration and loss of CO and Cl- to yield the 1,1,2-triphenylethyl cation and thence 1,1,2-triphenylethene by proton loss. However, ps and fs laser flash photolysis provides evidence that up to 25% of the alkene product stems from carbocation that arises directly from excited diazirine rather than from the carbene.

Original languageEnglish (US)
Pages (from-to)4807-4809
Number of pages3
JournalOrganic Letters
Volume8
Issue number21
DOIs
StatePublished - Oct 12 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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