Alkynes for electronic materials J Org Chem 1997 Chalifoux and - PowerPoint PPT Presentation

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 Strict geometric requirements in a crystal (Max Planck Inst.) 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 John D. Roberts (1897-1987) (Caltech)