Benzocyclobutene

BCB-based polymer dielectrics may be spun on or applied to various substrates for use in Micro Electro-Mechanical Systems (MEMS) and microelectronics processing.

Applications include wafer bonding, optical interconnects, low-κ dielectrics, or even intracortical neural implants.

Benzocyclobutene is a strained system which, upon heating to approximately 180 °C, causes the cyclobutene to undergo a conrotatory ring-opening reaction, forming o-xylylene.

Since this process destroys the aromaticity of the benzene ring, the reverse reaction is highly favored.

o-Xylylenes generated in this way have been used prolifically in cycloaddition reactions, which restore the aromaticity to the benzene ring, while forming a new annulated species.

Skeletal formula
Ball-and-stick model
Thermal generation of o-xylylene from benzocyclobutene
Thermal generation of o-xylylene from benzocyclobutene