15189-18-1

Basic information

• Product Name: 1-methyl-3-methylenecyclobutane
• Synonyms: 1-methyl-3-methylenecyclobutane
• CAS NO: 15189-18-1
• Molecular Weight: 82.1454
• Mol File: 15189-18-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-methyl-3-methylenecyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3-methylenecyclobutane(15189-18-1)
• EPA Substance Registry System: 1-methyl-3-methylenecyclobutane(15189-18-1)

Safety Data

• Hazardous Substances Data: 15189-18-1(Hazardous Substances Data)

Upstream product

• 10555-46-1 3-methylenecyclobutylmethyl bromide 

Downstream Products

• 1192-08-1 3-methylcyclobutan-1-one 
• 2398-10-9 trans-1,3-dimethylcyclobutane 

Relevant articles and documents

3-Methylenecyclobutyl, Cyclopent-3-enyl, and 3-Methylenecyclobutylmethyl Radicals; Absence of Homoallylic Conjugation

The 3-methylenecyclobutyl radical and the cyclopent-3-enyl radicals show such small e.s.r. hyperfine splittings from the δ- and γ-hydrogens respectively that homoallylic conjugation can be ruled out.Semiempirical SCF-MO calculations indicated that the through-space interaction of the p-orbital at Cα with the ?-orbitals is negligible because they are >2 Angstroem apart.The 3-methylenecyclobutylmethyl radical rearranges by β-scission to give the 2-allylallyl radicals.The Arrhenius parameters of the rearrangement were determined by kinetic e.s.r. spectroscopy and by study of the reduction of 3-methylenecyclobutylmethyl bromide with tri-n-butyltin hydride.The resonance stabilisation of the rearranged radical causes no significant lowering of the activation energy for β-scission.