Allene synthesis via C-C fragmentation: method and mechanistic insight.
A new method of allene synthesis is described. Suitably functionalized vinyl triflates undergo fragmentation to give allenes in high yield. Computational and experimental data provide a mechanistic framework for allene formation and the complementary formation of alkynes. The method is stereospecific.
Kolakowski
Robert V
RV
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Manpadi
Madhuri
M
Zhang
Yue
Y
Emge
Thomas J
TJ
Williams
Lawrence J
LJ
D000466:Alkadienes / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; D008698:Mesylates; C025947:propadiene