Cyclodecyne


Cyclodecyne is an organic compound with the chemical formula. The molecule has a ring of 10 carbon atoms, connected by nine single bonds and one triple bond.

Synthesis

Cyclodecyne was first synthesized and isolated in the mid-20th century as part of studies on medium-ring hydrocarbons. A common synthetic route involves the double dehydrohalogenation of 1,2-dibromocyclodecane using a strong base such as potassium hydroxide or sodium amide in a high-boiling solvent:
Alternatively, Fritsch–Buttenberg–Wiechell rearrangement of suitable dibromovinyl precursors has been used to generate cyclodecyne under milder conditions.

Physical properties

Due to its reactivity, cyclodecyne is often generated in situ and trapped in cycloaddition reactions rather than stored for long periods.