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 journalArticle

4 Citations (Scopus)

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

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Diazomethane
Photolysis
photolysis
fragmentation
Alkenes
carbenes
Carbon Monoxide
stems
alkenes
flash
Cations
Protons
Lasers
fragments
cations
protons
products
lasers
carbene

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Fragmentation of 2,2,2-triphenylethoxychlorocarbene : Evidence for ultrafast fragmentation-rearrangement in excited diazirines. / Fu, Xiaolin; Moss, Robert A.; Piotrowiak, Piotr; Myahkostupov, Mykhaylo; Gould, Ian.

In: Organic Letters, Vol. 8, No. 21, 12.10.2006, p. 4807-4809.

Research output: Contribution to journalArticle

Fu, Xiaolin ; Moss, Robert A. ; Piotrowiak, Piotr ; Myahkostupov, Mykhaylo ; Gould, Ian. / Fragmentation of 2,2,2-triphenylethoxychlorocarbene : Evidence for ultrafast fragmentation-rearrangement in excited diazirines. In: Organic Letters. 2006 ; Vol. 8, No. 21. pp. 4807-4809.
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