Alkynes for electronic materials
J Org Chem
1997
Chalifoux and Tykwinski
Nature Chem 2010
Strained alkynes
Yves Rubin (UCLA)
J Org Chem 1997
François Diederich
(Now at ETH Zürich)
Science 1993, 259, 1594
Classics in alkyne reactivity
1,3-dipolar cycloaddition
(recall ozonolysis!)
This is now an instrumental approach to
molecular diversification en route to
new molecules and new materials
Referred to as “click chemistry”
(Sharpless and Fokin, Scripps)
Rolf Huisgen
(Univ. Munich
Bio-orthogonal labelling of cells
Carolyn Bertozzi
(currently at Stanford)
Proc. Nat. Acad. Sci USA
2007, 104, 16793-97
Classics in alkyne reactivity
The Bergman cyclization:
A homolytic cascade that breaks
alkynes and leads to an aromatic
carbocycle. More later…
This reactivity has been used in
the “enediyne” anti-cancer drugs
Robert Bergman
(UC Berkeley)
Classics in alkyne reactivity
Topochemical polymerizations
Gerhard Wegner
(Max Planck Inst.)
Strict geometric requirements in a crystal
can promote a well-ordered polymer
process through very high energy
reactive intermediates.
And on the border … benzyne
Stoemer and Kahlert, 1902
Wittig, 1942
Roberts, 1953
More later …
Georg Wittig
(1897-1987)
John D. Roberts
(Caltech)