TY - JOUR
T1 - Fragmentation of 2,2,2-triphenylethoxychlorocarbene
T2 - Evidence for ultrafast fragmentation-rearrangement in excited diazirines
AU - Fu, Xiaolin
AU - Moss, Robert A.
AU - Piotrowiak, Piotr
AU - Myahkostupov, Mykhaylo
AU - Gould, Ian
PY - 2006/10/12
Y1 - 2006/10/12
N2 - (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.
AB - (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.
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U2 - 10.1021/ol061863l
DO - 10.1021/ol061863l
M3 - Article
C2 - 17020308
AN - SCOPUS:33750328822
SN - 1523-7060
VL - 8
SP - 4807
EP - 4809
JO - Organic Letters
JF - Organic Letters
IS - 21
ER -